(3S)-(+)-1-Benzyl-3-aminopyrrolidine → (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide

HRID 412635Notes

Reaction equation

HRID 412635 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([OH:18])=O.[CH2:19]([N:26]1[CH2:30][CH2:29][C@H:28]([NH2:31])[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:31][C@H:28]1[CH2:29][CH2:30][N:26]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:27]1)=[O:18]

Participants

3

Reactant 2

HCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidineHCID 12050655(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid

Product 1

HCID 9844164(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide

Procedure

The title compound was prepared by a similar method to Example 1 from (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylic acid [see Preparation 3] and (3S)-1-benzylpyrrolidin-3-ylamine. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 50:50:1, changing to 20:80:1, by volume, hexane:ethyl acetate:0.88 aqueous ammonia solution, in 10% increments. The product was further purified by recrystallisation from ethyl acetate:hexane to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide as a white solid.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 50:50:1
  2. customThe product was further purified by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-980d46f6ab554bad8a43ebed5c098681
Source dataset
uspto-grants-2003_05
Patent number
US06562964B1

Reaction notes

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