Methanol → HCID 68541571, compound

Participants

Reaction Conditions

Reaction Steps

Suspend (4-Bromobenzenesulfonyl)-acetonitrile (10.41 g, 40.02 mmol) in THF and cooled to 0° C., and add borane-dimethylsulfide complex (10 M, 12 mL, 120 mmol) to the suspension which is allowed to slowly warm to ambient temperature. The next day, quench the reaction with a slow addition of methanol until off-gassing ceases. Concentrate the reaction to dryness and add more methanol and bring to reflux for 3 hours. Concentrate the reaction to dryness, then dissolve in dichloromethane and extract with 1 N HCl (2×150 mL). Make the acidic aqueous extracts basic using 50% NaOH and Na2CO3. Treat the aqueous solution with dioxane (500 mL) and di-tertbutylcarbonate (10.91 g, 50.00 mmol) for 3 days. Dilute the reaction with dichloromethane, separate the layers and re-extract the aqueous with dichloromethane. Wash the organic extracts with aqueous saturated sodium chloride, dry over MgSO4, filter and concentrate to yield a crude oil. Chromatograph on silica utilizing (0→5→8%) ethyl acetate in dichloromethane to afford the title compound (4.20 g, 11.53 mmol). MS(ES), m/z 307/309 (M+1 minus t-butyl).

Provenance & Evidence