tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate → HCID 58714313, compound

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Reaction Steps

Following the procedure of Example 38, Step 3, (2R)-2-{[(2R)-pyrrolidin-2-yl)methyl]amino}-3-(4-chlorophenyl)-1-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)propan-1-one was prepared from (2R)-2-amino-3-(4-chlorophenyl)-1-(4-{2-[(methylsulfonyl)-amino]phenyl}piperazinyl)propan-1-one TFA salt (0.6 g, 1.1 mmol) in ClCH2Cl2Cl (10 mL), N-Boc-L-prolinal (Aldrich) (280 mg, 1.4 mmol), and NaBH(OAc)3 (Aldrich) (340 mg , 1.9 mmol). The desired compound (TFA salt) was purified by preparative TLC (60% Hexane, 38% CH2Cl2 and 2% 2N NH3 in MeOH), followed by preparative HPLC (TFA buffer) yielding a white solid (14.8 mg). MS (ESI, pos. ion) m/z: 520 (M+H); MS (ESI, neg. ion) m/z: 518 (M−H). Calc'd for C25H34ClN5O3S: 519.21.

Provenance & Evidence