1-Chloroethyl chloroformate → 3-(2,8-Bis(trifluoromethyl)-4-quinolinyl)-3-azetidinol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(2,8-bis(trifluoromethyl)-4-quinolinyl)-1-diphenylmethyl-3-azetidinol (690 mg, 1.37 mmol) in dichloroethane (20 mL), at 0° C., was added dropwise 1-chloroethyl chloroformate (0.18 mL, 1.2 eq). The mixture was stirred at 70° C. for 1 h and concentrated in vacuo. The residue was dissolved in MeOH (20 mL), stirred at room temperature for 17 h, concentrated in vacuo and the residue triturated with ether to give the title compound (351 mg, 69%) as a pale-yellow solid: mp 201° C. (dec); NMR δH (400 MHz, CDCl3) 4.44-4.45 (2H, m), 4.76-4.78 (2H, m), 7.95-7.99 (1H, m), 8.23 (1H, s), 8.38-8.42 (2H, m), 9.00 (1H, br s), 9.47 (1H, br s); Anal. Calcd for C14H11ClF6N2O: C, 45.12; H, 2.97; N, 7.51. Found: C, 45.21; H, 3.29; N, 7.08.

Provenance & Evidence