Diisobutylaluminum hydride → HCID 178516013, compound

Participants

Reaction Steps

To a suspension of trans-3-(4-hydroxyphenyl)-N-(4-phenylcyclohexyl)propionamide (0.65 g, 2.0 mmol) in toluene (5 mL), under a nitrogen atmosphere, was added DIBAL-H (12.0 mL of a 1 M in toluene, 12 mmol) with stirring. The reaction mixture was heated under reflux overnight. Additional DIBAL-H (12 mL of a 1.0 M solution in toluene, 12 mmol) was added, and heating was continued for a further 1.5 hours. The reaction mixture was cooled to room temperature and quenched by the slow addition of MeOH (50 mL). The mixture was heated at reflux for 15 minutes, cooled to room temperature, filtered, and concentrated under reduced pressure. Purification by flash chromatography (silica, 10% MeOH:CH2Cl2) then (silica, 89:10:1 CH2Cl2: MeOH:NH4OH) gave (b) trans 4-[3-(4-phenylcyclohexylamino)propyl]phenol (110 mg) as a tan solid: mp 211-214° C.; IR (KBr): 2926, 1516, cm−1; 1H NMR (300 MHz, CD3OD) δ 7.23-7.10 (m, 5H), 7.02 (d, J=8 Hz, 2H), 6.69 (d, J=8 Hz, 2H), 2.68-2.44 (m, 6H), 2.04 (br d, J=13 Hz, 2H), 1.88 (br d, J=13 Hz, 2H), 1.82-1.73 (m, 2H), 1.57 (dddd, J=13, 13, 13, 3 Hz, 2H), 1.26 (dddd, J=13, 13, 13, 3 Hz, 2H); CI—MS (methane) (m/z): 310 [M+H]+; HRMS-API (m/z): [M+H]+ calculated for C21H27NO, 310.2171; found, 310.2166; HPLC: method A, 7.93 minutes (95.2%); method B, 14.29 minutes (97.3%); Anal. Calcd. for C21H27NO.0.80H2O: C, 77.88; H, 8.90; N, 4.32. Found: C, 77.52; H, 8.66; N, 4.12.

Provenance & Evidence