(2R)-2-(Methoxymethyl)pyrrolidine → HCID 57959861, compound

Participants

Reaction Steps

To a solution of 2,4-dichloro-N-{2-oxo-1-[4-(propylsulphonyl)phenyl]-ethyl}benzamide (135 mg, 0.33 mmol) in 1,2-dichloroethane (5 mL) under nitrogen was added (R)-2-(methoxymethyl)pyrrolidine (81 □L, 0.66 mmol) followed by sodium triacetoxyborohydride (138 mg, 0.65 mmol) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched by addition of satd. NaHCO3(aq) and the product extracted into ethyl acetate (×2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated. One diastereoisomer of the title compound was isolated in pure form following preparative HPLC. 1H NMR δ (400 MHz, CDCl3) δ 1.00 (3H, t, J=7.4 Hz), 1.32-1.40 (1H, m), 1.52-1.59 (2H, m), 1.71-1.82 (4H, m), 1.96-2.04 (1H, m), 2.37-2.42 (1H, m), 2.87 (1H, br s), 3.00 (3H, s), 3.03-3.07 (2H, m), 3.21-3.35 (3H, m), 5.15-5.19 (1H, m), 7.34 (1H, dd, J=1.9, 8.3 Hz), 7.47 (1H, d, J=1.9 Hz), 7.59-7.61 (3H, m), 7.87 (2H, d, J=8.3 Hz), 8.31 (1H, d, J=5.3 Hz); m/z (ES+) 515 (M+H), 513 (M+H).

Provenance & Evidence