Methanol → (S)-3-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester

HRID 1020056Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([C:17]([OH:19])=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.CO.C(Cl)(=O)C([Cl:30])=O>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([C:17]([Cl:30])=[O:19])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 887Methanol

HCID 6228Dimethylformamide

HCID 65578Oxalyl chloride

HCID 736539(S)-1-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 7015654(S)-3-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester

Procedure

(S)-Piperidine-1,3-dicarboxylic acid 1-benzyl ester (XXXII) (12.0 g, 45.6 mmol) was taken in neat oxalyl chloride (30 ml), 0.2 mL of DMF was added and the mixture was stirred at room temperature for 1 hour. Completion of the reaction was monitored by TLC which showed the formation of a non-polar spot after treatment of a small amount with methanol. Then the reaction mixture was concentrated under reduced pressure to provide (S)-3-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester (XXXIII) (12.66 g) which was directly used in the next reaction.

Workup

concentrationThen the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-7123607617c747e096b004854c17292e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716296B2

Reaction notes

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