Methanol → 4-{[4-(3,4-Dichlorophenoxy)piperidin-1-yl]methyl}cyclopentane-1,2-diol

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Reaction Steps

The more polar isomer of 4-[[4-(3,4dichlorophenoxy)-1-piperidinyl]carbonyl]-1,2-cyclopentanediol (0.71 g) was dissolved in a solution of borane in tetrahydrofuran (16 mL of 1M solution) and the mixture was heated to reflux for 1.5 h. Methanol (10 mL) was added and the solution was heated under reflux for 1 h. The volatile components were evaporated and the residue was loaded onto an HPLC SCX cartridge in methanol and eluted with methanol, then with 0.7M ammonia in methanol to give the title compound (0.73 g) as an oil.

Provenance & Evidence