HCID 10692325, compound → HCID 22865010, compound

HRID 1078707Notes

Reaction equation

HRID 1078707 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[C].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:15])[CH3:16])[CH2:10][C@@H:9]1[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 10692325HCID 10692325, compound

Product 1

HCID 22865010HCID 22865010, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[(E)-2-ethoxycarbonylvinyl]pyrrolidine (29 g, 50 mmol) in ethanol (500 ml) was added 10% palladium-carbon catalyst (5 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 2 h. To the mixture was added an additional 10% palladium-carbon catalyst (2 g), and the mixture was stirred for 1.5 h under the same condition. The catalyst was filtered off, and the filtrate was concentrated in vacuo. The residue was subjected to silica gel column chromatography (heptane-ethyl acetate) to give (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(2-ethoxycarbonyl)ethylpyrrolidine (15.62 g, yield: 78%).

Workup

  1. stirringthe mixture was stirred for 1.5 h under the same condition
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6c8bca0003984389b345e5169404d932
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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