HCID 178484174, compound → HCID 178484183, compound

Participants

Reaction Steps

A solution of tert-butyl (S)-1-(trans-4-fluorocyclohexyl)-3-(N-(benzyloxycarbonyl)-N-methylamino)propan-2-ylcarbamate (550 mg, 1.3 mmol) in TFA/CH2Cl2 (20 mL, v/v 20%) was stirred for 1 h at rt, quenched with satd aq NaHCO3 until no further gas evolution was visible and extracted with CH2Cl2 (2×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and condensed under reduced pressure to obtain benzyl (S)-2-amino-3-(cis-4-fluorocyclohexyl)propylmethylcarbamate (400 mg, yield 95%). 1H NMR (CDCl3, 400 MHz) δ 1.42 (m, 4H), 1.64 (m, 4H), 2.98 (d, 3H), 3.21 (m, 1H), 3.50 (m, 1H), 3.90 (m, 1H), 5.13 (d, 2H), 7.33 (m, 5H).

Provenance & Evidence