1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide → 1-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide

HRID 267122Notes

Reaction equation

HRID 267122 reaction equation
C(OC([NH:11][C@@H:12]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@H:13]([OH:30])[CH2:14][N:15]1[CH:19]([C:20]([NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH:17]2[CH2:27][CH2:28][CH2:29][CH:16]12)=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@@H:12]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C@H:13]([OH:30])[CH2:14][N:15]1[CH:19]([C:20]([NH:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])[CH2:18][CH:17]2[CH2:27][CH2:28][CH2:29][CH:16]12

Participants

4

Reactant 1

HCID 572861401-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide

Product 1

HCID 186482401-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamideYield 87.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4.6 g of 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide (four diastereomers) in 90 ml of ethanol was hydrogenated over 10% palladium-on-carbon at 20° C. and under atmospheric pressure for 72 hours. The catalyst was removed by filtration and the filtrate was evaporated to give 2.958 g of 1-[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide (four diastereomers) as a brownish oil; MS: m/e 374 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-215ef89c6a1643b5869837cd57f399dc
Source dataset
uspto-grants-1997_07
Patent number
US05652369

Reaction notes

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