Butyl iodide → (3R,4R,5R)-3-benzyloxy-1-butyl-5-hydroxymethyl-4-piperidinol

Participants

Reaction Steps

(3R,4R,5R)-3-Benzyloxy-5-hydroxymethyl-4-piperidinol (87 mg, 0.37 mmol), 1-iodobutane (81 mg, 0.44 mmol, 50 μl), potassium carbonate (154 mg, 1.1 mmol) and dry acetone (8 ml) were stirred for 24h at 40° C. under a nitrogen atmosphere. The solvent was evaporated in vacuo, and the residue purified on a silica gel column (Eluent: ethyl acetate/methanol/25% ammonium hydroxide (6/1/1%)). This afforded the free base of (3R,4R,5R)-3-benzyloxy-1-butyl-5-hydroxymethyl-4-piperidinol (Yield: 72 mg, 67%).

Provenance & Evidence