Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Steps

5N HCl (4.7 mmol, 0.94 mL) was added to (3R,4R,5S)-1-benzyl-5-(chloromethyl)piperidine-3,4-diol (3) (5.1 mmol, 1.3 g) dissolved in EtOH. Solution was evaporated in vacuo and then co-evaporated 2-3× with EtOH. The residue was redissolved in EtOH and combined with Pd(OH)2 (0.27 g), and hydrogenated at 55 psi for 12 hrs. The catalyst was subsequently filtered through dicalite and the filtrate was evaporated to obtain crude (4) as an HCl salt. This was then chromatographed (5-15% MeOH/NH4OH (9:1) in CHCl3) to give 0.4 g of (4) as a white solid with MH+ of 165 and 1H NMR (DMSO-d6) 1.6 (m, 1H), 2.2 (m, 3H), 2.9 (m, 3H), 3.15 (m, 1H), 3.6 (m, 1H), 3.8 (dd, 1H), 4.68 (d, 1H), 4.88 (d, 1H).

Provenance & Evidence