Sodium borohydride → HCID 178479966, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-amino-2-methyl-4-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindol-1-one (1.35 g, 5.23 mmol) was dissolved in MeOH (30 mL), and cooled to 0° C., followed by addition of sodium borohydride (0.198 g, 5.23 mmol). The reaction mixture was stirred at 0° C. for 1 h. The reaction was quenched with sat. aq. NH4Cl, diluted with EtOAc, washed with brine, and dried over anhydrous sodium sulfate. The compound was purified on an Isco Combiflash eluting with 0 to 4% MeOH in EtOAc to afford the trans isomer and the cis isomer. Trans-isomer: 1H NMR (400 MHz, DMSO-d6) δ 7.05 (d, J=8.34 Hz, 1H), 6.51 (d, J=8.34 Hz, 1H), 5.83 (s, 2H), 4.53 (d, J=4.29 Hz, 1H), 4.33 (s, 2H), 3.38-3.48 (m, 1H), 2.98 (s, 3H), 2.28-2.38 (m, 1H), 1.90 (d, J=9.35 Hz, 2H), 1.68 (d, J=12.38 Hz, 2H), 1.38-1.51 (m, 2H), 1.19-1.32 (m, 2H); MS (ES+): m/z: 262.1674 [MH+]. HPLC: tR=0.98 min (UPLC TOF MS: polar—3 min). Cis-isomer: 1H NMR (400 MHz, DMSO-d6) δ 7.07 (d, J=8.34 Hz, 1H), 6.54 (d, J=8.34 Hz, 1H), 5.83 (s, 2H), 4.33 (s, 3H), 2.99 (s, 3H), 2.34-2.43 (m, 1H), 1.70-1.87 (m, 4H), 1.38-1.57 (m, 4H); MS (ES+): m/z: 262.1693 [MH+]. HPLC: tR=1.04 min (UPLC TOF MS: polar—3 min).

Provenance & Evidence