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

HRID 1010563Notes

Reaction equation

HRID 1010563 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-8d3baf5dce114a699c08afdc76681bd1
Source dataset
uspto-grants-2011_07
Patent number
US07977327B2

Reaction notes

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