HCID 57190117, compound → HCID 10621099, compound

HRID 1492821Notes

Reaction equation

HRID 1492821 reaction equation
[O:1]([C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([CH:21]=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10]1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]>C(O)C.[C].[Pd]>[O:1]([C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C@H:11]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10]1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 57190117HCID 57190117, compound

Product 1

HCID 10621099HCID 10621099, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Ethyl 3-[(2S,4R)-4-tert-butyldimethylsiloxy-N-tert-butoxycarbonylpyrrolidin-2-yl]acrylate (10 g, 26.8 mmol) was subjected to catalytic hydrogenation in ethanol (200 ml) by means of 10% palladium carbon (500 mg) at 60° C. for 3 hours. The reaction solution was left to cool, and the catalyst was filtered off. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (Wakogel™ C-300, 300 ml, ethyl acetate-hexane 1:10) to obtain ethyl 3-[(2R,4R)-4-tert-butyldimethylsiloxy-N-tert-butoxycarbonylpyrrolidin-2-yl]propionate (9.91 g, yield: 98%).

Workup

  1. waitThe reaction solution was left
  2. temperatureto cool
  3. filtrationthe catalyst was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7748dc9f26484b738fb3c31edb225c04
Source dataset
uspto-grants-1994_12
Patent number
US05374720

Reaction notes

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