Methyl iodide → (4aR,5R,8S,8aR)-5-[(4-fluorophenyl)amino]-8-(methoxymethyl)hexahydro-2H-chromen-4a(5H)-ol

Participants

Reaction Steps

Dissolved 95 mg (4aS,5R,8S,8aR)-5-[(4-fluorophenyl)amino]-8-(hydroxymethyl)hexahydro-2H-chromen-4a(5H)-ol in 2.1 mL THF then added 39 mg NaH. The reaction was stirred for 1.5 hours at RT, then diluted with an additional 1 mL of THF before adding 50 uL iodomethane. The reaction was stirred overnight at RT, then added to sat. NH4Cl. The mixture was diluted with water and extracted with CH2Cl2. The crude extract was dried over Na2SO4 then filtered, concentrated, then purified on silica gel to provide the title compound. 3H NMR (500 MHz, CDCl3) δ=1.34-1.40 (m, 2H), 1.54-1.62 (m, 2H), 1.72-1.77 (m, 1H), 1.78-1.87 (m, 1H), 2.10-2.16 (m, 1H), 2.22-2.30 (m, 1H), 2.32-2.42 (m, 1H), 3.29 (dd, J1=9.3 Hz, J2=6.6 Hz, 1H), 3.31-3.33 (m, 1H), 3.44-3.50 (m, 2H), 3.53 (bd, J=11.2 Hz), 4.09 (dd, Jz=11.6 Hz, J2=6.5 Hz, 1H), 4.58 (d, J=11.2 Hz) ppm. HRMS (ES) m/z calc'd: 310.1813. found 310.1811.

Provenance & Evidence