(3S)-(+)-1-Benzyl-3-aminopyrrolidine → Ammonia

HRID 841948Notes

Reaction equation

HRID 841948 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C:23]([OH:25])=O)=O)(C)(C)C.C(N1CC[C@H](N)C1)C1C=CC=CC=1>>[NH3:8].[CH2:19]1[CH:18]2[C:23](=[O:25])[N:8]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[N:10]=[C:9]3[N:17]2[CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidineHCID 59063201(2S)-1-[1-(tert-butoxycarbonyl)-1H-1,3-benzimidazol-2-yl]-2-piperidinecarboxylic acid

Product 2

HCID 222AmmoniaHCID 185383821,3,4,1 2a-tetrahydropyrido[1',2':3,4]imidazo[1,2-a][1,3]benzimidazol-12(2H)-one

Procedure

The title compound was prepared by a similar method to Example 1 from (2S)-1-[1-(tert-butoxycarbonyl)-1H-1,3-benzimidazol-2-yl]-2-piperidinecarboxylic acid [see Preparation 48] and (3S)-1-benzylpyrrolidin-3-ylamine. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 70:30 changing to 50:50, by volume, hexane:ethyl acetate followed by 90:10:1, dichloromethane:methanol: 0.88 ammonia to afford 1,3,4,1 2a-tetrahydropyrido[1′,2′:3,4]imidazo[1,2-a][1,3]benzimidazol-12(2H)-one as a white solid.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 70:30 changing to 50:50, by volume, hexane

Sources & evidence

ORD record
ord-dc35efed3dfb462c816d8c1c4b530f5e
Source dataset
uspto-grants-2002_04
Patent number
US06372736B1

Reaction notes

Loading…