Trifluoroacetic acid → HCID 21480573, compound

Participants

Reaction Steps

3,4,5,6,7,8-Hexahydro-3-hydroxymethyl-6-((4-methoxyphenyl)methyl)quinolin-2[1H]-one (6.75 g) (prepared according to Example 17) was suspended in triethylsilane (35 ml) and TFA (17.25) ml was added with rapid stirring. When tlc (SiO2 /EtOAc) showed no starting material remained, the stirring was stopped and the reaction mixture separated into two layers. The lower (TFA) layer was added to a saturated solution of sodium carbonate and this organic solution was extracted into dichloromethane, dried (MgSO4) and evaporated. The residue (9.4 g) was purified in several fractions to give 3,4,4a,5,6,7,8,8a-octahydro-3-hydroxymethyl-6-((4-methoxyphenyl)methyl)quinolin-2[1H]-one (mixed isomers 4.58 g). This product was purified by chromatography on a "Dynamax" 60A Si 21×250 mm column using 0.25% NH4OH, 1.8% MeOH in dichloromethane as mobile phase. A flow rate of 21.6 ml/min was used and injections of 10 ml of 10 mg/ml of product in mobile phase were made. The material eluting at 20.1 minutes was collected and recrystallised from ethyl acetate to give the title compound (0.2 g) mp 196°-197° C.

Provenance & Evidence