(3S,4S)-tert-butyl 4-(4-(benzyloxy)-3-fluorophenyl)-3-hydroxypiperidine-1-carboxylate → (3S,4S)-tert-butyl 4-(3-fluoro-4-hydroxyphenyl)-3-hydroxypiperidine-1-carboxylate

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Reaction Steps

To (3S,4S)-tert-butyl 4-(4-(benzyloxy)-3-fluorophenyl)-3-hydroxypiperidine-1-carboxylate (4.0 g, 9.96 mmol, E-2 from step C) in degassed MeOH (100 mL) was added 10% Pd/C (0.191 g, 1.79 mmol) and the reaction was repeated evacuated and flushed with hydrogen gas. Then placed under 1 atm of hydrogen for 4 h. The reaction solution was purged with nitrogen and filtered through celite. The filtrated was concentrated to afford (3S,4S)-tert-butyl 4-(3-fluoro-4-hydroxyphenyl)-3-hydroxypiperidine-1-carboxylate (2.99 g, 96% yield) as a grey oil. LC-MS [M+H]+−tBu=256.05; 1H NMR (500 MHz, DMSO-d6) δ 7.03-6.95 (m, 1H), 6.89-6.78 (m, 2H), 4.78 (d, J=4.6 Hz, 1H), 4.09 (br. s., 2H), 3.94 (br. s., 1H), 3.36 (dd, J=9.5, 4.7 Hz, 1H), 3.17 (s, 1H), 2.80-2.58 (m, 1H), 2.42-2.27 (m, 1H), 1.65 (dd, J=13.4, 3.4 Hz, 1H), 1.56-1.33 (m, 10H).

Provenance & Evidence