(3S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine → (3S)-3-(tert-Butoxycarbonyl)amino-4-ethylpyrrolidine

HRID 1010567Notes

Reaction equation

HRID 1010567 reaction equation
C(OC([N:11]1[CH2:15][CH:14]([CH:16]=[CH2:17])[C@H:13]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>[C].[Pd].C(O)C>[C:22]([O:21][C:19]([NH:18][C@H:13]1[CH:14]([CH2:16][CH3:17])[CH2:15][NH:11][CH2:12]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 67307498(3S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 67308068(3S)-3-(tert-Butoxycarbonyl)amino-4-ethylpyrrolidine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A 10% palladium carbon catalyst (15 mg) was added to a solution of (3S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine [an isomer mixture of (4S)-form: (4R)-form (1:4)] (230 mg, 0.66 mmol) in ethanol (8 mL), followed by stirring in a hydrogen atmosphere under an ordinary pressure at room temperature for 12 hours. After filtration, the filtrate was concentrated under reduced pressure, to thereby yield the title compound (an isomer mixture of (4S)-form and (4R)-form (1:4)) as a colorless oily substance (148 mg, 100%).

Workup

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

Sources & evidence

ORD record
ord-d6b8a10bf00641bfbdcaff2196a365d5
Source dataset
uspto-grants-2011_07
Patent number
US07977327B2

Reaction notes

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