Allyl bromide → HCID 57814144, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2-((3S,4S)-4-hydroxy-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-ylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide (50 mg, 0.1 mmol) in DMF (1 mL), was added NaH (17 mg, 0.4 mmol) at 0° C. The mixture was stirred at 0° C. for 10 min., followed by addition of allyl bromide (0.011 mL, 0.13 mmol). The mixture was stirred at 0° C. for 30 min., and the organic phase was washed with water, dried over MgSO4, concentrated, and subjected to flash chromatography (EtOAc:MeOH:Et3N 9:1:0.1) to generate the title compound (6 mg, 10% yield). 1H-NMR (CDCl3) δ: 1.40-1.57 (m, 2H), 1.70-1.90 (m, 2H), 2.27-2.40 (m, 2H), 2.70-2.82 (m, 2H), 3.30-3.42 (m, 3H), 3.77-3.85 (m, 1H), 3.90-4.05 (m, 3H), 4.06-4.22 (m, 3H), 4.29-4.32 (m, 1H), 5.10-5.30 (m, 2H), 5.80-5.98 (m, 1H), 6.60 (d, J=8.1 Hz, 1H), 7.10 (s, 1H), 7.57 (t, J=8.1 Hz, 1H), 7.77 (d, J=7.2 Hz, 1H), 8.00 (d, J=5.4 Hz, 1H), 8.08 (s, 1H). MS m/z: 456 (M+1)

Provenance & Evidence