Ethanol → HCID 59384346, compound

Participants

Reaction Steps

Diethyl 2-(tert-butoxycarbonylamino)-2-(5-(4-(octyloxy)-3-(trifluoromethyl)-phenyl)-pyridin-2-yl)malonate 5a (110 mg, 0.176 mmol, 1.0 equiv) in THF (2.0 mL) was added LiBH4 (57 mg, 2.64 mmol, 15.0 equiv) at 0° C., followed by addition of ethanol (0.8 mL) carefully. The resultant was warmed up to room temperature for 10 minutes. LC-MS indicated the completion of the reaction. The reaction was terminated by addition of water. Extraction with ethyl acetate and the organic layer was washed with brine and dried over sodium sulfate and condensed. The residue (crude reduction product with significant decarboxylation) was treated with 2M HCl in THF to afford the title compound after preparative HPLC purification. MS (ESI, M+H+)=411.1; 1H NMR (400 MHz, DMSO-d6) δ 8.95 (d, 1H, J=2.4 Hz), 8.39 (s, 3H), 8.22 (dd, 1H, J=8.4 Hz, J=2.4 Hz), 8.01 (dd, 1H, J=8.4 Hz, J=2.0 Hz), 7.93 (d, 1H, J=2.0 Hz), 7.60 (d, 1H, J=8.4 Hz), 7.39 (d, 1H, J=9.2 Hz), 5.48 (br, 1H), 4.48 (br, 1H), 4.17 (t, 2H, J=6.0 Hz), 3.86-3.72 (m, 2H), 1.75 (m, 2H), 1.44 (m, 2H), 1.29 (m, 8H), 0.86 (t, 3H, J=6.8 Hz).

Provenance & Evidence