Diisopropylethylamine → 1-Benzyl-3(SR)-(4-(N-(benzyloxycarbonyl)-N-sec-butylamino)-piperidin-1-ylmethyl)-4-(SR)-phenylpyrrolidine

Participants

Reaction Steps

The title compound was prepared from 20 mg of 1-Benzyl-3-(SR)-formyl-4-(SR)-phenylpyrrolidine, 24 mg of 4-(N-(benzyloxycarbonyl)-N-secbutylamino)piperidine-hydrochloride, 0.013 mL of DIEA and 24 mg of sodium triacetoxyborohydride using a procedure analogous to that described in Example 9, Step B to provide 32 mg of the title compound. HPLC (YMC "Octyl" 4.6×250 mm column, 60:40 v/v H2O/CH3CN+0.5% TFA, 1.5 mL/min, 200 nm): Retention Time: 12.99 min. 1H NMR (300 MHz, CDCl3): δ0.70-0.82 (m, 3H), 1.16 (t, J =6.4 Hz, 3H), 1.37-1.95 (m, 10H), 2.34-2.66 (m, 6H), 2.83-2.99 (m, 4H), 3.69 (ABq, J =13 Hz, 2H), 5.11 (s, 2H), 7.14-7.39 (m, 15H). Mass Spectrum (ESI): 540.6 (M+H).

Provenance & Evidence