Sodium Cyanide → [(S)-2-(7-Cyanomethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl ester

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Reaction Steps

A solution of the product from Example 2, Step B (0.55 g, 1.45 mmol) in dichloromethane (20 mL) was cooled (ice bath), thionyl chloride (0.16 mL, 2.18 mmol) was added, and the mixture was stirred for thirty minutes. The reaction mixture was evaporated to a residue which was dissolved in dichloromethane (20 mL) and evaporated. A solution of sodium cyanide (0.29 g, 5.8 mmol) in DMSO (10 mL) was added to this residue and the mixture was stirred at room temperature for one hour. Saturated aqueous sodium bicarbonate (100 mL) was added and the mixture was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with saturated aqueous sodium bicarbonate (2×150 mL), dried (MgSO4) and evaporated to a tan solid (0.49 g, 87%): LC/MS m/z 389 [M+H]+.

Provenance & Evidence