(2R,4R)-1-Benzyloxycarbonyl-2-(3-t-butoxycarbonylmethylidenepropyl)-4-t-butyldimethylsilyloxypyrrolidine → (2R,4R)-2-(4-t-butoxycarbonylbutyl)-4-t-butyldimethylsilyloxypyrrolidine

HRID 1088281Notes

Reaction equation

HRID 1088281 reaction equation
C(OC([N:11]1[CH2:15][C@H:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:13][C@H:12]1[CH2:24][CH2:25][CH:26]=[CH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[C:31]([O:30][C:28]([CH2:27][CH2:26][CH2:25][CH2:24][C@@H:12]1[CH2:13][C@@H:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])[CH2:15][NH:11]1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

4

Reactant 1

HCID 54121397(2R,4R)-1-Benzyloxycarbonyl-2-(3-t-butoxycarbonylmethylidenepropyl)-4-t-butyldimethylsilyloxypyrrolidine

Product 1

HCID 15671521(2R,4R)-2-(4-t-butoxycarbonylbutyl)-4-t-butyldimethylsilyloxypyrrolidine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(2R,4R)-1-Benzyloxycarbonyl-2-(3-t-butoxycarbonylmethylidenepropyl)-4-t-butyldimethylsilyloxypyrrolidine (1.17 g) was dissolved in 24 ml of ethanol, and 350 mg of 5% palladium carbon was added thereto, followed by hydrogenation at room temperature under 1 atm for 3 hours. The catalyst was removed by filtration, and the filtrate was distilled to obtain (2R,4R)-2-(4-t-butoxycarbonylbutyl)-4-t-butyldimethylsilyloxypyrrolidine.

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe filtrate was distilled

Sources & evidence

ORD record
ord-e3d9a37e1c7b49a48c2e1d68e0057866
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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