(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-cyclopropylpyrrolidine → (3S,4S)-3-(tert-Butoxycarbonyl)amino-4-cyclopropylpyrrolidine

HRID 1253425Notes

Reaction equation

HRID 1253425 reaction equation
C(OC([N:11]1[CH2:15][C@H:14]([CH:16]2[CH2:18][CH2:17]2)[C@H:13]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>[C].[Pd].C(O)C>[C:23]([O:22][C:20]([NH:19][C@H:13]1[C@@H:14]([CH:16]2[CH2:17][CH2:18]2)[CH2:15][NH:11][CH2:12]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 53837949(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-cyclopropylpyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 22871839(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-cyclopropylpyrrolidine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A 10% palladium carbon catalyst (50 mg) was added to a solution of (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-cyclopropylpyrrolidine (408 mg, 1.13 mmol) in ethanol (5 mL), followed by stirring in a hydrogen atmosphere under an ordinary pressure at 45° C. for 12 hours. After filtration, the filtrate was concentrated under reduced pressure, to thereby yield the title compound as a colorless oily substance (255 mg, quantitative amount). The product was employed, without further purification, in the subsequent step.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d4911e7d4bac4430ba9aef083d0e662c
Source dataset
uspto-grants-2013_06
Patent number
US08455482B2

Reaction notes

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