water acetonitrile CCl4 → 2-(Tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

Participants

Reaction Steps

To a solution of (3R)-tert-butyl 3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate (D32) (440 mg, 2.06 mmol) in a mixture MeCN/CCl4/H2O (6/6/9 ml), sodium periodate (1.76 g, 8.25 mmol) was added and the reaction stirred vigorously for 5 min before addition of Ruthenium trichloride (12.8 mg, 0.062 mmol). The resulting solution was stirred 18 hrs at RT then quenched by addition of isopropanol (6 ml). The resulting black mixture was diluted with Et2O (50 ml) and filtered through a celite pad. The filtrate was evaporated and the residue was dissolved in water, the pH was adjusted to pH˜9-10 with K2CO3 and the aqueous was washed with Et2O (3×30 ml). Aqueous was then acidified to pH˜4-5 and re-extracted with EtOAc (3×30 ml). Collected organics after solvent evaporation afforded the title compound (D33) (216 mg).

Provenance & Evidence