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

HRID 1253419Notes

Reaction equation

HRID 1253419 reaction equation
C(OC([N:11]1[CH2:15][C@H:14]([CH2:16][CH3:17])[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].CO>[C:22]([O:21][C:19]([NH:18][C@H:13]1[C@@H: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 59665274(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-ethylpyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 10512827(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-ethylpyrrolidine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A 10% palladium carbon catalyst (50 mg) was added to a solution of (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-ethylpyrrolidine (514 mg, 1.48 mmol) in methanol (15 mL). The resultant mixture was stirred at room temperature for 2 hours under an ordinary pressure in a hydrogen atmosphere. After filtration, the filtrate was concentrated under reduced pressure, to thereby yield the title compound as a colorless oily substance (324 mg, quantitative amount).

Workup

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

Sources & evidence

ORD record
ord-54c2227300f8463794d9e18b81498ad6
Source dataset
uspto-grants-2013_06
Patent number
US08455482B2

Reaction notes

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