HCID 24727994, compound → (3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pyrrolidine

HRID 37996Notes

Reaction equation

HRID 37996 reaction equation
C([N:8]1[CH2:12][C@@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:10]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[Si:14]([O:13][C@H:11]1[C@H:10]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[CH2:9][NH:8][CH2:12]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

4

Reactant 1

HCID 24727994HCID 24727994, compound

Product 1

HCID 24727995(3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pyrrolidineYield 99.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of (3R,4R)-1-benzyl-3,4-bis(tert-butyldimethylsilyloxy)pyrrolidine (13.4 g, 31.8 mmol) and Pd(OH)2/C (2.23 g, 3.18 mmol, 20%) in MeOH (134 mL) was stirred for 20 h under H2 atmosphere (balloon). The reaction mixture was filtered through a Celite plug and concentrated under reduced pressure to afford 10.5 g (91%) of the crude (3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pyrrolidine that was used directly without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite plug
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-598c1dd6a4a24db08e28e6b20c4cf0e0
Source dataset
uspto-grants-2013_09
Patent number
US08524702B2

Reaction notes

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