Water → HCID 86694782, compound

Participants

Reaction Steps

Add H2O (4 mg, 0.25 mmol) and TMSCl (27 mg, 0.25 mmol) to a solution of (1R,2R,3S,4S,5S)-3-(3-hydroxyphenyl)-2,6,6-trimethyl-4-((methyl(phenethyl)amino)methyl)bicyclo[3.1.1]heptan-3-ol (100 mg, 0.25 mmol) in 2-butanone (5 mL). Stir the reaction mixture at room temperature for 3 hours. After removal solvent by evaporation, wash the residue with EtOAc (1 mL×2) and dry under vacuum to give (1R,2R,3S,4S,5S)-3-(3-hydroxyphenyl)-2,6,6-trimethyl-4-((methyl(phenethyl)amino)methyl)bicyclo[3.1.1]heptan-3-ol hydrochloride (93 mg, Yield: 85.3%) as white solid. 1H NMR (400 MHz, D2O) δ 7.21-7.32 (m, 7H), 7.97-7.99 (d, J=7.2, 1H), 6.71-6.78 (dd, J1=8.0, J2=22.0, 1H), 2.86-3.33 (m, 5H), 2.43-2.68 (m, 7H), 2.11-2.20 (m, 2H), 1.73-1.75 (m, 1H), 1.23-1.25 (d, J=5.6, 3H), 1.04-1.05 (d, J=4.4, 3H), 0.69-0.71 (d, J=5.6, 3H). [α]D20=−8.6 (c=1.4 mg/mL, MeOH).

Provenance & Evidence