1-(Benzyloxycarbonyl)-3-(tert-butyldimethylsilyloxymethyl)piperidine → Tert-butyl-dimethyl-(3-piperidylmethoxy)silane

HRID 602124Notes

Reaction equation

HRID 602124 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>[Pd].CO>[Si:19]([O:18][CH2:17][CH:13]1[CH2:14][CH2:15][CH2:16][NH:11][CH2:12]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 589926311-(Benzyloxycarbonyl)-3-(tert-butyldimethylsilyloxymethyl)piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 58992622Tert-butyl-dimethyl-(3-piperidylmethoxy)silaneYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% palladium on activated carbon (1.32 g) was added to 1-(benzyloxycarbonyl)-3-(tert-butyldimethylsilyloxymethyl)piperidine (13.2 g, 36.3 mmol) in methanol (130 mL). The mixture was stirred at room temperature for 1 hour in a hydrogen atmosphere. Subsequently, the mixture was filtered through Celite, followed by evaporation of the solvent to give 7.96 g (96%) of the desired compound as a colorless oil.

Workup

  1. filtrationSubsequently, the mixture was filtered through Celite
  2. customfollowed by evaporation of the solvent

Sources & evidence

ORD record
ord-0b0a62a655e34190b0f76ee0e67e51cb
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

Loading…