Water → (1S)-2-amino-1-phenylethan-1-ol

A mixture of 2.6 g of lithium aluminum hydride in 400 ml of tetrahydrofuran was cooled in an ice-acetone bath, and a solution of 9.4 g of 2(S)-t-butyldimethyl-silyloxy-2-phenylethylazide [prepared as described in step (c) above] in 100 ml of tetrahydrofuran was added dropwise to the cooled mixture. The mixture was stirred for 1 hour, whilst ice-cooling, after which 2.6 ml of water, 2.6 ml of a 15% w/v aqueous solution of sodium hydroxide and 7.8 ml of water were added dropwise to the reaction mixture, in that order. Insoluble materials were filtered off, and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:2 by volume mixture of ethyl acetate and ethanol as the eluent, to give the title compound as crystals, melting at 69°-70° C.

1. temperaturewas cooled in an ice-acetone bath
2. temperaturecooling
3. filtrationInsoluble materials were filtered off
4. concentrationthe filtrate was concentrated by evaporation under reduced pressure
5. customThe resulting residue was purified by column chromatography through silica gel
6. additionby volume mixture of ethyl acetate and ethanol as the eluent

ORD record

ord-d6fd42277a074273a37473fd400c1a01

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05576340