Benzyl Alcohol → HCID 71227049, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methyl-1-(4-nitrophenyl)piperidine-3-carboxamide (1.8538 g, 7.04 mmol) and phenylmethanol (7.61 g, 70.4 mmol) in C1CH2CH2Cl (30 ml) cooled at 0° C. was added 1,8-diazabicyclo[5.4.0]undec-7-ene (3.18 mL, 21.12 mmol) dropwise, followed by 1-bromopyrrolidine-2,5-dione (1.378 g, 7.74 mmol) in portions. After addition, the resulting yellow mixture was stirred at 0° C. for 15 min, then at rt for 3.5 hrs, LCMS showed the reaction was not complete and 10% more of NBS (138 mg) was added and the reaction was allowed to stir for an additional 2.5 hrs. The reaction mixture was quenched by addition of water (50 mL) and then adjusted to pH=5 with 1N aqueous HCl. The solution was extracted with EtOAc (3×). The combined EtOAc extracts were washed with water, saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-30% EtOAc/Hex to give product, benzyl 3-methyl-1-(4-nitrophenyl)piperidin-3-ylcarbamate (2.274 g, 6.16 mmol, 87% yield) as a yellow oil. Anal. Calcd. for C20H23N3O4 m/z 369.4, found: 370.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 8.06 (d, J=9.34 Hz, 2 H), 7.37 (d, J=4.40 Hz, 1 H), 7.34-7.27 (m, 4 H), 6.81 (d, J=9.34 Hz, 2 H), 5.09-4.93 (m, 2 H), 4.74 (s, 1 H), 4.18-4.07 (m, 1 H), 3.74-3.62 (m, 1 H), 3.11-3.02 (m, 2 H), 2.04-1.99 (m, 1 H), 1.81-1.68 (m, 2 H), 1.58-1.51 (m, 1 H), 1.44 (s, 3 H).

Provenance & Evidence