US 8,476,470 B2 · Process for production of bicyclo[2.2.2]octylamine derivative

Abstract

The present invention herein provides a process for production of a bicyclo[2.2.2]octylamine derivative which may be used as an intermediate for preparation of medical and pharmaceutical products. The process is quite efficient and can produce the derivative in a large-scale while using mild reaction conditions. The process for producing a bicyclo[2.2.2]octylamine derivative comprises the steps of subjecting, to ring-formation, a compound represented by the following general formula (1): [wherein R1 represents an alkyl group having 1 to 6 carbon atoms, which may have a substituent; an arylmethyl group which may have a substituent; or an arylethyl group which may have a substituent], and a compound represented by the following general formula (2): R2—NH2 (2) [wherein R2 represents an alkyl group having 1 to 6 carbon atoms, which may have a substituent; an aralkyl group which may have a substituent; a hydroxyl group; an alkyloxy group having 1 to 6 carbon atoms, which may have a substituent; or an aralkyloxy group which may have a substituent], and then reducing the resulting product.

Claims10

Dependent claims

A process for production of a compound represented by the following general formula (4) comprising the following steps:

(Step1) a step for reacting a compound represented by the following general formula (1):
[in the formula (1), R1 represents an alkyl group having 1 to 6 carbon atoms, which may have a substituent;
an arylmethyl group which may have a substituent;
or an arylethyl group which may have a substituent], with a compound represented by the following general formula (2):
R2—NH2 (2)
[in the formula (2), R2 represents an alkyl group having 1 to 6 carbon atoms, which may have a substituent;
an aralkyl group which may have a substituent;
a hydroxyl group;
an alkyloxy group having 1 to 6 carbon atoms, which may have a substituent;
or an aralkyloxy group which may have a substituent], to thus form a compound represented by the following general formula (3):
[in the formula (3), R1 and R2 are the same as those defined above];
and
(Step 2) a step for hydrolyzing the compound represented by the general formula (3) to form a compound represented by the following general formula (4):
[in the formula (4), R1 and R2 are the same as those defined above].

11 more elements

A process for production of a compound represented by the following general formula (8) comprising the following steps:

(Step 3) a step for reducing a compound represented by the following general formula (4):
[in the formula (4), R1 represents an alkyl group having 1 to 6 carbon atoms, which may have a substituent;
an arylmethyl group which may have a substituent;
or an arylethyl group which may have a substituent;
and
R2 represents an alkyl group having 1 to 6 carbon atoms, which may have a substituent;
an aralkyl group which may have a substituent;
a hydroxyl group;
an alkyloxy group having 1 to 6 carbon atoms, which may have a substituent;
or an aralkyloxy group which may have a substituent], to thus form a compound represented by the following general formula (5):
[in the formula (5), R1 and R2 are the same as those defined above];
(Step 4) a step for reacting the compound represented by the general formula (5) with a halogenating agent, an alkylsulfonating agent having 1 to 6 carbon atoms, which may have a substituent, or a benzenesulfonating agent which may have a substituent, to thus form a compound represented by the following general formula (6):
[in the formula (6), X represents a halogen atom, an alkylsulfonyloxy group having 1 to 6 carbon atoms, which may have a substituent, or a benzenesulfonyloxy group which may have a substituent;
and
R1 and R2 are the same as those defined above];
(Step 5) a step for eliminating the substituent X present on the compound represented by the general formula (6) to thus form a compound represented by the following general formula (7):
[in the formula (7), R1 and R2 are the same as those defined above];
and
(Step 6) a step for reducing the compound represented by the general formula (7) to thus form a compound represented by the following general formula (8):
[in the formula (8), R3 represents a hydrogen atom;
an alkyl group having 1 to 6 carbon atoms, which may have a substituent;
or an aralkyl group which may have a substituent;
and
R1 is the same as that defined above].

21 more elements

A process for production of a compound represented by the following general formula (8) comprising the following steps:

(Step 1) a step for reacting a compound represented by the following general formula (1):
[in the formula (1), R1 represents an alkyl group having 1 to 6 carbon atoms, which may have a substituent;
an arylmethyl group which may have a substituent;
or an arylethyl group which may have a substituent], with a compound represented by the following general formula (2):
R2—NH2 (2)
[in the formula (2), R2 represents an alkyl group having 1 to 6 carbon atoms, which may have a substituent;
an aralkyl group which may have a substituent;
a hydroxyl group;
an alkyloxy group having 1 to 6 carbon atoms, which may have a substituent;
or an aralkyloxy group which may have a substituent], to thus form a compound represented by the following general formula (3):
[in the formula (3), R1 and R2 are the same as those defined above];
(Step 2) a step for hydrolyzing the compound represented by the general formula (3) to form a compound represented by the following general formula (4):
[in the formula (4), R1 and R2 are the same as those defined above];
(Step 3) a step for reducing the compound represented by the general formula (4) to thus form a compound represented by the following general formula (5):
[in the formula (5), R1 and R2 are the same as those defined above];
(Step 4) a step for reacting the compound represented by the general formula (5) with a halogenating agent, an alkylsulfonating agent having 1 to 6 carbon atoms, which may have a substituent, or a benzenesulfonating agent which may have a substituent to thus form a compound represented by the following general formula (6):
[in the formula (6), X represents a halogen atom, an alkylsulfonyloxy group having 1 to 6 carbon atoms, which may have a substituent, or a benzenesulfonyloxy group which may have a substituent;
and
R1 and R2 are the same as those defined above];
(Step 5) a step for eliminating the substituent X present on the compound represented by the general formula (6) to thus form a compound represented by the following general formula (7):
[in the formula (7), R1 and R2 are the same as those defined above];
and
(Step 6) a step for reducing the compound represented by the general formula (7) to thus form a compound represented by the following general formula (8):
[in the formula (8), R3 represents a hydrogen atom;
an alkyl group having 1 to 6 carbon atoms, which may have a substituent;
or an aralkyl group which may have a substituent;
and
R1 is the same as that defined above].

25 more elements

Dependencies are inferred from the claim text.

Process for production of bicyclo[2.2.2]octylamine derivative

Life of this patent

Process for production of bicyclo[2.2.2]octylamine derivative

Life of this patent

Abstract

Claims10