Sodium borohydride → HCID 58495491, compound

Participants

Reaction Conditions

Reaction Steps

Add cobalt(II) chloride hexahydrate (1.83 mg, 7.7 mmol) to a solution of 4-(2,2-dimethylpropane-sulfonylmethyl)-benzonitrile (966 mg, 3.85 mmol) in methanol (25 mL). Cool the mixture to 0° C. and stir for 15 min. Carefully add sodium borohydride (1.46 g, 38.49 mmol) in small batches, allow the mixture to warm to room temperature and stir for 2 h. Dilute the mixture with water and partition between water and chloroform. Extract the aqueous phase three times with chloroform/iso-propanol (3:1). Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (80 g) eluting with DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 35 min, 85:15; 50 mL/min) to give the title compound (181 mg, 49%). MS (APCI+) m/z: 256 (M+H)+.

Provenance & Evidence