US 10,703,719 B2Granted

Method for producing 5-hydroxypiperidine-2-carboxylic acid

AssigneeApi Corporation

InventorsJun Takehara, Masato Murai, Takashi Ohtani, Tomoko Maeda, Tsugihiko Hidaka

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Abstract

A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid represented by the formula (10) below: the method including removing the protecting group from the hydroxyl group in a compound represented by formula (7) below: (wherein P represents a protecting group, R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms) to synthesize a compound represented by formula (8) below: (wherein R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms).

Claims13

Dependent claims

A compound

represented by formula (6a) below:
wherein X represents Cl, Br, or I, P′ represents a tetrahydropyranyl group, methoxymethyl group, ethoxyethyl group, tert-butyl group, or tert-butyldimethylsilyl group, and R3 represents an alkyl group containing 1 to 4 carbon atoms, and A represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or an aralkyloxy group containing 7 to 20 carbon atoms,
or a compound represented by formula (4a) below:
wherein X represents Cl, Br, or I, P′ represents a tetrahydropyranyl group, methoxymethyl group, ethoxyethyl group, or tert-butyldimethylsilyl group, and R2 represents an alkyl group containing 1 to 10 carbon atoms, an aryl group containing 6 to 12 carbon atoms, or an aralkyl group containing 7 to 20 carbon atoms,
or a compound represented by formula (3a) below:
wherein X represents Cl, Br, or I, and P′ represents a tetrahydropyranyl group, methoxymethyl group, or ethoxyethyl group,
or a compound represented by formula (2a) below:
wherein X represents Cl, R1 represents a hydrogen atom or an optionally substituted alkyl group containing 1 to 4 carbon atoms, P″ represents a tetrahydropyranyl group or ethoxyethyl group.

5 more elements

Dependencies are inferred from the claim text.

Facts

Application: 15/965,289Filed 27 Apr 2018 · division
Priority: JP 2013-27276627 Dec 2013
Published: US 2018/0002286 A130 Aug 2018
Granted: 7 Jul 2020
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 211/60
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
C07C 233/47
With the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom: having the carbon atom of…
C07C 309/66
Of a saturated carbon skeleton: methanesulfonates
C07D 498/08
In which the condensed system contains two hetero rings: bridged systems

Family

PCT/JP2014/084518Parent of this division · filed 26 Dec 2014
Application15/705,349Parent of this division · filed 15 Sep 2017
US 9,790,181 B2Parent of this division · filed 17 Oct 2017
US 2018/0244619 A1Pre-grant publication · published 30 Aug 2018
US 9,988,351 B2Parent of this division
Application15/108,141Parent of this division
US 2016/0318867 A1Published application
US 2018/0002286 A1Published application
US 10,703,719 B2This patent

From the US filing history. Foreign family members aren’t listed.