tert-Butyl methyl ether → HCID 68499756, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.500 g of methyl 2-oxo-1-(trimethylsilanylethoxymethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-9-carboxylate in 35 ml of tetrahydrofuran is admixed with 0.205 g of lithium borohydride. The reaction mixture is stirred at 50° C. over 4 hours and subsequently poured onto 300 ml of a 1:1 mixture of saturated aqueous sodium hydrogencarbonate solution and tert-butyl methyl ether. The phases are separated and the aqueous phase is extracted with 150 ml of tert-butyl methyl ether. The combined organic phases are washed with 150 ml of water, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow resin from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (1:1 EtOAc-heptane); Rt=4.38.

Provenance & Evidence