1,2-Dichloroethane → Tert-butyl{(cis)-2-[(2,2,2-trifluoroethyl)carbamoyl]cyclohexyl}carbamate

Participants

Reaction Steps

To a mixture of cis-2-tertbutoxycarbonylamino-cyclohexanecarboxylic acid (Acros, 2 g, 8.22 mmol), 2,2,2-trifluoroethylamine (0.969 mL, 12.33 mmol), HOBT (1.888 g, 12.33 mmol) and DIPEA (4.31 mL, 24.66 mmol) in DMF (10 mL) was added EDC (2.364 g, 12.33 mmol) and the mixture allowed to stir at RT for 1 hr. The reaction was quenched into 10% aq. KHSO4 (100 mL) and product extracted with ethyl acetate (100 mL). Organic washed with aq. NaHCO3 (50 mL) and then brine (50 mL). Aqueous extracts backwashed with ethyl acetate (50 mL) and organic extracts combined, dried over sodium sulfate, filtered and concentrated to give 2.55 gm of a white solid, I-5a. 1H NMR (600 MHz, CDCl3) δ 6.18 (m, 1H), 5.07 (m, 1H), 3.75-4.0 (m 3H), 2.62 (m, 1H), 1.3-2.0 (br m, 8H), 1.40 (s, 9H).

Provenance & Evidence