Sodium borohydride → HCID 178471782, compound

Participants

Reaction Steps

To a stirred solution of ethyl [trans-4-({ethyl[2-formyl-4-(trifluoromethyl)phenyl]amino}methyl)cyclohexyl]acetate (Step A; 153 mg; 0.38 mmol) in EtOH (1 mL) was added sodium borohydride (7.3 mg; 0.19 mmol). The reaction stirred at room temperature for 1 h and was concentrated in vacuo. The residue was redissolved in EtOAc (10 mL) and washed with sat. NH4Cl (10 mL). The aqueous layer was re-extracted with EtOAc (2×10 mL) and the combined organic layers were washed with H2O and brine (10 mL each), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient) to afford ethyl [trans-4-({ethyl[2-(hydroxymethyl)-4-(trifluoromethyl)phenyl]amino}methyl)cyclohexyl]acetate as a yellow oil. LCMS=402.2 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 7.56-7.54 (m, 2 H), 7.29-7.26 (m, 1 H), 4.85 (s, 2 H), 4.13 (q, J=7.1 Hz, 2 H), 3.10-3.02 (m, 2 H), 2.91-2.85 (m, 2 H), 2.17 (d, J=6.9 Hz, 2 H), 1.84-1.70 (m, 4 H), 1.57-1.44 (m, 2 H), 1.39-1.31 (m, 1 H), 1.26 (t, J=7.1 Hz, 3 H), 1.08-1.04 (m, 3 H), 1.01-0.93 (m, 3 H).

Provenance & Evidence