Sodium borohydride → HCID 58295720, compound

Participants

Reaction Steps

To a stirred solution of (E)-7-bromo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indene-1,4′-piperidin]-3(2H)-one (20 mg, 0.042 mmol) in MeOH (2 mL) and THF (2 mL) was added solid NaBH4 (12 mg). The mixture was stirred at rt for 3 h. The mixture was diluted with 10% aq citric acid and extracted with ether (2×30 mL). The combined ether extracts were dried over MgSO4 and concentrated. The residue was purified by prep HPLC to afford (±)-(E)-1-(7-bromo-3-hydroxy-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-yl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one (1.8 mg, 9%) as a solid. LC-MS Method 1 tR=1.83, min, m/z=480, 482; 1H NMR (CDCl3) 1.39 (m, 2H), 1.63 (m, 1H), 2.12 (m, 1H), 2.5-3.0 (4H), 3.36 (m, 1H), 4.16 (m, 1H), 4.82 (m, 1H), 5.23 (br s, 1H), 6.86 (d, 1H), 7.18 (m, 1H), 7.3-7.8 (6H), 7.95 (d, 1H).

Provenance & Evidence