(3R,5R,6S,7S)-7-(Benzyloxymethyl)-6-(4-fluorophenyl)-3-(-2-methoxy-5-(trifluoromethyl)phenyl)-1-oxaspiro[4.4]nonane → (3R,5R,6S,7S)-(6-(4-Fluorophenyl)-3-(-2-methoxy-5-(trifluoromethyl)phenyl)-1-oxaspiro[4.4]non-7-yl)methanol

Participants

Reaction Steps

(3R,5R,6S,7S)-7-(Benzyloxymethyl)-6-(4-fluorophenyl)-3-(-2-methoxy-5-(trifluoromethyl)phenyl)-1-oxaspiro[4.4]nonane (2.4 mg, 0.0047 mmol) was stirred with 0.7 mg of 20% palladium(II) hydroxide m 0.5 mL of 95% ethanol under hydrogen at atmospheric pressure for 1.5 h. The mixture was filtered through a 0.45 micron filter and the catalyst was rinsed with additional 95% ethanol. The filtrate was evaporated to give 1.6 mg of the title compound. 1NMR (400 MHz, CDCl3): δ 7.43-7.32 (m, 4H), 7.03 (t, 2H, J=9 Hz ), 6.80 (d, 1H, J=9 Hz ), 3.75 (s, 3H), 3.72 (t, 1H, J 8 Hz ), 3.65-3.58 (m, 2H), 3.48 (dd, 1H, J=10, 5 Hz ), 2.82 (quintet, 1H, J=8 Hz ), 2.73-2.58 (m, 2H), 2.23 (dd, 1H, J=12, 8 Hz ), 2.18-2.02 (m, 3H), 1.99-1.88 (m, 1H), 1.66-1.54 (m, 1H). Mass spectrum (EI): m/z=424.1 (M+).

Provenance & Evidence