3-Bromo-1-propanol → HCID 67415421, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(3-chloro-4-hydroxy-5-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (800 mg, 2.05 mmol, Intermediate 14) in isopropanol (30 mL) and 2 N aq. NaOH (10 mL) is treated with 3-bromopropanol (569 mg, 4.09 mmol). The dark red reaction mixture is stirred at 70° C. After 4.5 and 22 h another portion of 3-bromopropanol (569 mg, 4.09 mmol) is added. Stirring is continued for further 2 h after the last addition. The solvent is removed under reduced pressure and the residue is dissolved in EA and washed twice with water. The organic layer is dried over MgSO4 and evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 1:1 to give 3-[3-chloro-4-(3-hydroxy-propoxy)-5-methoxy-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (460 mg) as a yellow oil; LC-MS: tR=1.10 min, [M+1]+=449.22; 1H NMR (CDCl3): δ 676-674 (m, 1H), 6.64-6.61 (m, 1H), 4.05 (t, J=5.5 Hz, 2H), 3.90-3.85 (m, 2H), 3.77 (s, 3H), 3.01-2.85 (m, 5H), 2.72 (d, J=18.8 Hz, 1H), 2.31 (s, 3H), 1.98-1.90 (m, 2H), 1.85-1.80 (m, 2H), 1.05 (s, 3H), 0.63 (s, 3H).

Provenance & Evidence