Sodium Hydroxide → HCID 53691393, compound

Participants

Reaction Steps

To a solution of lithium aluminum hydride (30 ml of a 1M solution in tetrahydrofuran diluted to 130 ml with tetrahydrofuran) was added aluminum chloride (3.94 g). The mixture was stirred for 30 mins and then 1,3,4a,5,6,7-hexahydro-2H-quino[4,3,2-ef][1,4]benzthiazepin-2-one (6.65 g) was added. The reaction mixture was stirred for 1 hr and then poured into 60 ml of 10% sodium hydroxide solution. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were washed with water, saturated sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was preadsorbed on silica and purified by flash chromatography (2% triethylamine/ethyl acetate) to give 3.0 g (48%) of product, mp 171°-175° C. Recrystallization from methanol/water gave the analytical sample, mp 175°-177° C.

Provenance & Evidence