Enamines and diastereo-selective reduction of enamines
AssigneeAllergan, Inc.
InventorsDanny T. Dinh, William R. Perrault
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Abstract
Described herein is a compound having a chemical structure of Formula A: wherein m, p, q, W, Z, Y, X1, X2, R1, R2, R3 and R4 are as defined herein. A diastereo-selective reduction of the compound comprising contacting the compound of Formula A with a reducing agent in an aprotic polar or non-polar solvent is also described.
Claims32
An isolated compound of Formula A:
- wherein:
- m is 1 or 2;
- p is 0, 1, or 2;
- q is 0;
- W is C;
- Z is CH2;
- Y is NH, O, S, or CH2;
- X1 and X2 are hydrocarbons which together contain a total of five to nine carbon atoms and which link together such that the moiety:
- forms a bridged bicyclic ring system;
- R1, R2 and R3 are independently H or C1-3 alkyl;
- R4 is H, C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, C3-6 cycloalkyl, or C3-6 cycloalkenyl, each of the alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl is optionally substituted with at least one group selected from OH, halo, CN, C1-3 alkoxy, and NH2.
An isolated compound which is selected from the following compounds:
An isolated compound which is selected from the following compounds
An isolated compound which is selected from the following compounds
A method of synthesizing a compound of Formula B or a salt thereof, comprising:
- contacting an isolated compound of Formula A with a reducing agent in an aprotic polar or non-polar solvent optionally comprising an acid
- and, optionally, purifying the compound of Formula B, wherein the compound of Formula B is:
- or a salt thereof, and wherein the compound of Formula A is:
An isolated compound which is:
Dependencies are inferred from the claim text.