Piperidin-4-ol → 1-Benzyl-3-(SR)-(4-hydroxypiperidin-1-ylmethyl)-4-(SR)-phenyl-pyrrolidine

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Reaction Steps

The title compound was prepared from 500 mg of 1-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine, 196 mg of 4-hydroxypiperidine and 597 mg of sodium triacetoxyborohydride using a procedure analogous to that described in Example 9, Step B to provide 348 mg of the title compound. RF : 0.16 (5% MeOH in CH2Cl3). 1H NMR (300 MHz, CDCl3): δ1.35-1.54 (m, 2H), 1.69-1.83 (m, 2H), 1.93-2.05 (m, 2H), 2.36-2.71 (m, 7H), 3.89-3.01 (m, 3H), 3.55-3.72 (m, 3H), 7.14-7.38 (m, 10H). Mass Spectrum (NH3 -CI): 351.3 (M+H).

Provenance & Evidence