HCID 22855968, compound → HCID 10621099, compound

HRID 2399398Notes

Reaction equation

HRID 2399398 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].[H][H]>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

5

Reactant 2

HCID 22855968HCID 22855968, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 10621099HCID 10621099, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of (2R,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[(E)-2-ethoxycarbonylvinyl]-pyrrolidine (20 g, 50 mmol) in ethanol (500 ml) was added 10% palladium-carbon (5 g), and the mixture was stirred under atmospheric pressure in a hydrogen atmosphere at room temperature for 2 h. Further, 10% palladium-carbon (2 g) was added thereto, and the mixture was stirred under atmospheric pressure in a hydrogen atmosphere at room temperature for 1.5 h. The catalyst was filtered off, and the solvent was removed in vacuo. The residue was subjected to silica gel column chromatography (Wakogel™ C-300, heptane-ethyl acetate) to give (2R,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(2-ethoxycarbonylethyl)pyrrolidine (15.62 g, yield: 78%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c9ce553da4bf4d5baafebd220d009cb1
Source dataset
uspto-grants-1995_09
Patent number
US05449672

Reaction notes

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