Ethyl 5-(4-chlorobenzyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-4-acetate → 5-(4-Chlorobenzyl)-4-(2-hydroxyethyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole

Participants

Reaction Conditions

Reaction Steps

To a solution of product from Step 3 (785 mg, 1.83 mmol) in THF (30 mL), cooled to 0° C. and under N2 atmosphere, there was added LiAlH4 (152 mg, 4 mmol). The resulting mixture was stirred at 0° C. for 30 minutes, then quenched carefully with ice-cold H2O, and acidified with 1N aq HCl (10 mL). The mixture was extracted twice with Et2O, and these extracts were washed 3× with brine, dried over Na2SO4, and evaporated. The residue was chromatographed, eluting with a 1:1 mixture of EtOAc and hexane, to afford the title product as a thick oil.

Provenance & Evidence