Sodium triacetoxyborohydride → HCID 24877154, compound

Participants

Reaction Steps

(2S)N-Cyclopropyl-N-[1-(2-methylcarbonylpropylamino-4-methylpentanoyl)piperidin-3-yl]-3-trifluoromethylbenzenesulfonamide (20) was prepared as follows. A solution of compound 8 prepared in Example 2 (100 mg, 0.22 mmol), compound 19 (12 mg, 0.22 mmol, Aldrich) and 4 Å molecular sieves (500 mg) in 2 mL of 1,2-dichloroethane (DCE) was shaken at room temperature for 10 minutes, and then NaB(OAc)3H (43 mg, 0.22 mmol) was charged. The resulting mixture was shaken at room temperature for 24 hours. The reaction mixture was quenched with MeOH (0.2 mL), water (2 mL) was added and the mixture was extracted with DCM (3×4 mL). The organic layers were combined and washed with brine, dried over Na2SO3, concentrated under vacuum and purified by column (silica gel, EtOAc, then EtOAc/MeOH 10/1) to give the title compound 20 as white solid (40 mg, yield 32%). 1H NMR (400 MHz, CD3OD): δ 8.01-8.26 (m, 3H), 7.86-7.93 (m, 1H), 5.0-5.15 (m, 0.4H), 4.45-4.55 (m, 1.2H), 3.75-4.35 (m, 1.3H), 2.55-3.45 (m, 5H), 0.75-2.20 (m, 26H); LC: 98%; MS: m/z=568 (M+Na+).

Provenance & Evidence