Potassium Carbonate → HCID 86009475, compound

Participants

Reaction Conditions

Reaction Steps

1-(4-Benzenesulfonyl-4-methylpentyl)-4-ethoxycarbonylpiperidine (0.3 g, 0.79 mmol) was dissolved in dichloromethane (5 ml) and cooled to −78° C. Diisobutylaluminium hydride (1.0M in dichloromethane, 1.0 ml, 1.0 mmol) was added. The reaction was stirred for 30 minutes at −78° C. then quenched by the addition of ethyl acetate (0.5 ml) and water (0.1 ml). The mixture was stirred at room temperature for 10 minutes then filtered through Celite. The filtrate was concentrated in vacuo. The residue was dissolved in methanol (20 ml). Dimethyl (1-diazo-2-oxopropyl)phosphonate (0.3 g, 1.56 mmol) and potassium carbonate (0.23 g, 1.65 mmol) were added and the reaction stirred at room temperature for 1 hour. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and brine. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 2–4% methanol/dichloromethane, to give the title compound (90 mg, 34%). NMR of hydrochloride salt:

Provenance & Evidence