Benzyl N-(2-t-Butyldimethylsilyloxy-1-methylethyl)-carbamate → (S)-2-Amino-tert-butyldimethylsilyloxypropane

HRID 1901674Notes

Reaction equation

HRID 1901674 reaction equation
[H][H].[Si:3]([O:10][CH2:11][CH:12]([NH:14]C(=O)OCC1C=CC=CC=1)[CH3:13])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>[Pd].C(O)C>[Si:3]([O:10][CH2:11][CH:12]([NH2:14])[CH3:13])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 14308419Benzyl N-(2-t-Butyldimethylsilyloxy-1-methylethyl)-carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 21474737(S)-2-Amino-tert-butyldimethylsilyloxypropaneYield 80.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogen was introduced into a mixture of 4.0 g of benzyl N-(2-t-butyldimethylsilyloxy-1-methylethyl)carbamate (prepared as described in Preparation 8), 0.80 g of 10% w/w palladium-on-carbon and 40 ml of ethanol for 1 hour. At the end of this time, the atmosphere was replaced by nitrogen, the palladium-on-carbon was removed by filtration from the reaction mixture, and the filtrate was concentrated by evaporation under reduced pressure, to give 1.88 g of the title compound having an Rf value of 0.27 (on silica gel thin layer chromatography, using a 1:3 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customthe palladium-on-carbon was removed by filtration from the reaction mixture
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-a325df8f00034bbbadfbcb310d1603c6
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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