反应详情

A −78° C. suspension of 3-((1S)-2-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}-1-hydroxyethyl)-4-(3,4-dimethylphenyl)-2-methyl-1(2H)-isoquinolinone (12 mg, 0.021 mmol) and amberlyst 15 resin (6 mg, 0.036 mmol) in Dichloromethane (DCM) (290 μl) was treated with isobutylene until the volume approximately doubled. The reaction mixture was sealed and allowed to warm to ambient temperature. After 48 h, the reaction mixture was cooled to −78° C. and then opened to the atmosphere. The reaction mixture was filtered through a short pad of silica and rinsed with EtOAc. The filtrate was concentrated in vacuo. The residue was dissolved in Tetrahydrofuran (THF) (290 μl) and treated with 1.0 M TBAF in THF (145 μl, 0.145 mmol). After 2 h, the reaction mixture was filtered through a short pad of silica gel and washed with EtOAc. The filtrate was concentrated in vacuo and purified by reverse phase hplc to afford the title compound (6 mg, 0.016 mmol, 43.6% yield) as a white solid: Rt=1.02, ES+ MS: 380 (M+1).

1. customThe reaction mixture was sealed
2. temperaturethe reaction mixture was cooled to −78° C.
3. filtrationThe reaction mixture was filtered through a short pad of silica
4. washrinsed with EtOAc
5. concentrationThe filtrate was concentrated in vacuo
6. dissolutionThe residue was dissolved in Tetrahydrofuran (THF) (290 μl)
7. waitAfter 2 h
8. filtrationthe reaction mixture was filtered through a short pad of silica gel
9. washwashed with EtOAc
10. concentrationThe filtrate was concentrated in vacuo
11. custompurified by reverse phase