Chloroethane → HCID 21070310, compound

Participants

Reaction Steps

A mixture of 0.489 g of the compound obtained in step A of Example 17 and 0.086 g of azetidine hydrochloride and 116 μl of TEA in 15 ml of MeOH is stirred for 1 hour at RT. Next, 0.072 ml of AcOH is added, the mixture is stirred for 15 minutes at RT, 0.079 g of sodium cyanoborohydride is added and the mixture is stirred for 2 hours at RT. The reaction mixture is concentrated under vacuum, the residue is extracted with DCM, the organic phase is washed with saturated NaHCO3 solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture (95/5; v/v) and then a DCM/MeOH/NH4OH mixture (95/5/0.5; v/v/v). The product obtained is dissolved in EtOAc, acidified to pH 1 by adding hydrochloric ether and diluted with ether, and the precipitate formed is filtered off by suction. 0.115 g of the expected product is obtained.

Provenance & Evidence