Benzyl N-[2-t-Butyldimethylsilyloxy-1(R)-methylethyl]carbamate → (R)-1-((tert-butyldimethylsilyl)oxy)propan-2-amine

HRID 1901684Notes

Reaction equation

HRID 1901684 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([NH:12]C(=O)OCC1C=CC=CC=1)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[Pd].C(O)C>[Si:1]([O:8][CH2:9][C@H:10]([NH2:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22867577Benzyl N-[2-t-Butyldimethylsilyloxy-1(R)-methylethyl]carbamate

Product 1

HCID 22867570(R)-1-((tert-butyldimethylsilyl)oxy)propan-2-amineYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A procedure similar to that described in Preparation 9 was repeated, except that 16.4 g of benzyl N-[2-t-butyldimethylsilyloxy-1(R)-methylethyl]carbamate (prepared as described in Preparation 24), 3.5 g of 10% w/w palladium-on-carbon and 100 ml of ethanol were used, to give 8.55 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) and having [α]D =-10.1° (methanol, c=1.155).

Workup

  1. customA procedure similar to that described in Preparation 9

Sources & evidence

ORD record
ord-eb8179fb4b7a4f70b04cab6d037f4fa6
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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