HCID 14308420, compound → (s)-1-(Tert-butyldimethylsilyloxy)propan-2-amine

HRID 2294309Notes

Reaction equation

HRID 2294309 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 14308420HCID 14308420, compound

Product 1

HCID 10954330(s)-1-(Tert-butyldimethylsilyloxy)propan-2-amineYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A procedure similar to that described in Preparation 9 was repeated, except that 10.22 g of benzyl N-[2-t-butyldimethylsilyloxy-1(S)-methylethyl]carbamate (prepared as described in Preparation 32), 2.00 g of 10% w/w palladium-on-carbon and 80 ml of ethanol were used, to give 5.69 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 =+9.7° (methanol, c=1.040).

Workup

  1. customA procedure similar to that described in Preparation 9

Sources & evidence

ORD record
ord-8f24990b71a448e988d789fb65bac0fc
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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