Triethylamine → 3-Pyrrolidinol, 1-[1-(diphenylmethyl)-3-azetidinyl]-

Participants

Reaction Steps

1-(Diphenylmethyl)azetidin-3-yl methanesulfonate (see J. Org. Chem.; 56; 1991; 6729; 310 mg, 0.98 mmol) was dissolved in acetonitrile (3.5 mL). Pyrrolidin-3-ol (104 mg, 1.2 mmol) and triethylamine (124 mg, 1.2 mmol) were added and the mixture was subjected to microwave single node heating for 10 minutes. The solvent was removed by evaporation and the residue was dissolved in ethyl acetate. The solution was washed with water, dried over MgSO4 and then the solvent was evaporated. There was obtained 280 mg (93%) of 1-[1-(diphenylmethyl)azetidin-3-yl]pyrrolidin-3-ol as an oil. 1H NMR (300 MHz, CDCl3): 1.6-1.8 (m, 1H), 2.1-2.3 (m, 2H), 2.4-2.6 (m, 2H), 2.6-2.8 (m, 1H), 2.9-3.0 (m, 2H), 3.1-3.2 (m, 1H), 3.3-3.4 (m, 2H), 4.3 (m, 1H), 4.4 (s, 1H), 7.1-7.5 (m, 10H); LCMS: m/z 309 (M+1)+.

Provenance & Evidence