Water → HCID 67148555, compound

Participants

Reaction Steps

Treat a 0° C. mixture of 4-(tert-butyl-diphenyl-silanyloxy)-1-cyanomethyl-cyclohexanecarboxylic acid ethyl ester (7.19 g, 15.9 mmol), cobalt (II) chloride hexahydrate (1.90 g, 7.98 mmol) in THF (130 mL), and water (65 mL) portion-wise with sodium borohydride (3.02 g, 7.98 mmol). Warm to room temperature and stir for 16 hours under N2. Heat the reaction to 50° C. for 8 hours, cool to room temperature and stir 16 hours under N2. Treat the reaction with 28% ammonium hydroxide (2 mL) and filter through hyflo. Remove the solvent from the filtrate in vacuo and dilute the residue with minimal water and brine and extract three times with 3:1 chloroform:isopropanol. Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford crude product. Purify with a 0 to 10% methanol in CH2Cl2 gradient on silica gel to afford 1.20 g (18%) of the titled product. Rf=0.48 and 0.61 (9/1 CH2Cl2/methanol). MS (m/z): 408 (M+).

Provenance & Evidence