Diiodomethane → 5-Azaspiro[2.5]octane-5-carboxylic acid, phenylmethyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Diethyl zinc (1.38 g, 11.2 ml, 1 M solution in hexane 11.24 mmol) in dichloromethane (10 ml) was added trifluoroacetic acid (1.28 g, 0.84 ml, 11.24 mmol) drop wise manner at 0° C. Diiodomethane (3.01 g, 0.90 ml, 11.24 mmol) in dichloromethane (5 ml) was added and reaction mixture was stirred at 0° C. for 30 min. A solution of benzyl 3-methylenepiperidine-1-carboxylate (prepared according to the procedure given in European Journal of Medicinal Chemistry 1991, 26, 625-631), (1.3 g, 5.62 mmol) in dichloromethane (10 ml) was added and reaction mixture stirred at 0° C. for 30 min and then at 25° C. for 18 hr. The progress of reaction was monitored by TLC. Reaction mixture was diluted with dichloromethane (25 ml) and poured in to a saturated solution of sodium bicarbonate (50 ml). Solid precipitated out was filtered, organic layer was separated and dried over sodium sulphate and concentrated under reduced pressure to obtain a crude product, which was purified by flash column chromatography using 6% ethyl acetate in hexanes to obtain the title compound (0.95 g, 68.9%). MS: m/z 246 (M+1).

Provenance & Evidence