Ammonium formate → tert-Butyl ((1S,5R,6S)-3-azabicyclo[3.3.0]octan-6-yl)carbamate

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Reaction Conditions

Reaction Steps

tert-Butyl(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylcarbamate (100 mg, 0.316 mmol) from Step A and ammonium formate (100 mg, 1.580 mmol) were combined in ethanol. The reaction was deoxygenated at low temperature, and palladium on carbon (3.36 mg, 0.032 mmol) was added. The reaction was heated to reflux under nitrogen. After 3 hours, TLC and LCMS showed mostly starting material. Degussa's catalyst and 5 equivalents more ammonium formate were added and the reaction mixture was refluxed under nitrogen overnight. More ammonium formate and Degussa's catalyst were added and the reaction heated to 90° C. After 2 hours, TLC and LCMS showed no remaining starting material. The reaction was filtered through diatomaceous earth containing carbonate functionalized silica gel (Silicycle, Quebec, Canada) with methanol. Solvent removal in vacuo gave tert-butyl(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylcarbamate: MS (ESI+) m/z 226 (M+H)+.

Provenance & Evidence