tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate → 1-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidine

HRID 1173172Notes

Reaction equation

HRID 1173172 reaction equation
C([NH:8][C@@H:9]1[C@@H:13]([OH:14])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:8][C@@H:9]1[C@@H:13]([OH:14])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1

Participants

4

Reactant 1

HCID 11277777tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 104654571-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidineYield 98.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of the intermediate (5.4 g, 18.5 mmol) of step B, Pd(OH)2/C (0.3 g) in MeOH (200 mL) was stirred under hydrogen at 55 psi overnight. The catalyst was filtered off and the filtrate was concentrated to give 3.7 g of the desired product as a solid. MS calculated (M+H)+ 203, found 203.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a218dfc0f8f4446480512e9e1ec6e953
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Reaction notes

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