N-tert-butyloxycarbon l-3-azabic clo[3.3.0]octane synthesis

Yield:-

Reaction Conditions:

with dmap;triethylamine in dichloromethane at 0; for 2 h;

Steps:

2.3

Step 3; [0107] The material from Step 2 was dissolved in ethanol (25mL) and hydrogenated over10%Pd on carbon (1.2gm) for 18 hours at atmospheric pressure. The mixture was filtered through a pad of celite, acidified with IN hydrochloric acid, and evaporated to dryness under reduced pressure. This product was taken up into dichloromethane (15OmL) and treated successively with di-tert-butyl dicarbonate (12.5gm, 1.2eq), dimethylaminopyridine (40mgm) and triethylamine (17.5mL, 2.2eq) at 0⁰C. After two hours at O⁰C the reaction mixture was diluted with ethyl acetate, and washed successively with IN hydrochloric acid, water, brine, and then dried over anhydrous sodium sulfate. Evaporation of the organic layer under reduced pressure gave crude product, which was purified by silica gel chromatography, eluting with 5% ethyl acetate/hexane, to provide N-tert-butyloxycarbonyl- octahydrocyclopenta-[c]pyrrole (7.69gm).

References:

WO2009/55467,2009,A2 Location in patent:Page/Page column 31