Ammonium formate → HCID 86722342, compound

Participants

Reaction Conditions

Reaction Steps

A flask with stir bar, condenser and nitrogen line was charged with rac-(4aR,11bS)—N-(diphenylmethylene)-11b-ethyl-1,2,4,4a,5,6,7,11b-octahydrospiro[dibenzo[a,c][7]annulene-3,2′-[1,3]dioxolan]-9-amine (21, R2=Ethyl) (0.550 g, 1.181 mmol), 10% Pd on carbon (0.094 g, 0.089 mmol) and MeOH (25 mL). Ammonium formate (1.12 g, 17.7 mmol) was added and the mixture was heated to about 65° C. After about 15 min the mixture was cooled to rt and filtered through a pad of Celite®. The pad was washed with MeOH (15 mL) then the filtrate was concentrated under reduced pressure. The residue was partitioned between EtOAc (20 mL), water (5 mL) and sat. aq. NaHCO3 (15 mL). The layers were separated and the aqueous layer was extracted with EtOAc (15 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to yield rac-(4aR,11bS)-11b-ethyl-1,2,4,4a,5,6,7,11b-octahydrospiro[dibenzo[a,c][7]annulene-3,2′-[1,3]dioxolan]-9-amine (22, R2=Ethyl) (0.345 g, 97%); LC/MS, method 3, Rt=2.50 min, MS m/z 302 (M+H)+. 1H NMR (400 MHz, DMSO) δ 6.83 (d, J=8.3 Hz, 1H), 6.36-6.28 (m, 2H), 4.75 (bs, 2H), 3.87-3.72 (m, 4H), 2.82-2.75 (m, 1H), 2.57-2.45 (m, 1H), 2.30-2.26 (m, 1H), 2.14-2.05 (m, 1H), 2.00-1.89 (m, 2H), 1.72-1.15 (m, 9H), 0.58 (t, J=7.4 Hz, 3H).

Provenance & Evidence