Hydrochloric Acid → 2-(1-Methyl-3,4-dihydroisoquinolin-5-yl)propan-2-ol

温度

100 °C

1-(1-methyl-3,4-dihydroisoquinolin-5-yl)ethanone. A solution of 5-iodo-1-methyl-3,4-dihydroisoquinoline (2.0 g, 7.38 mmol), Pd(OAc)2 (41 mg, 0.184 mmol) and DPPP (85 mg, 0.207 mmol) in dry DMSO (15 mL) was degassed, and butylvinyl ether (4.80 mL, 36.9 mmol) and Et3N (1.24 mL, 8.85 mmol) were then added in succession. The reaction was heated to 100° C. for 18 h, and then allowed to cool to RT. The mixture was diluted with Et2O and washed with H2O. The organic phase was then dried over Na2SO4, filtered and concentrated in vacuo to give a brown oil that was taken up in THF (50 mL) and treated with a 2N aq. solution of HCl (25 mL). The mixture was stirred at RT for 4 h, and then diluted with AcOEt and washed with H2O. The aq. phase was then neutralized and rendered basic by adding Na2CO3, and then extracted with AcOEt. The combined org. layers were then dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, DCM to DCM/MeOH 9:1) to provide the title compound (1.06 g) as a brown oil, which was used as it is in the next step. UPLC-MS: MS 188.0 (M+H+); UPLC rt 0.45 min.

1. temperatureto cool to RT
2. washwashed with H2O
3. dry with materialThe organic phase was then dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto give a brown oil that
7. washwashed with H2O
8. additionby adding Na2CO3
9. extractionextracted with AcOEt
10. dry with materiallayers were then dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customThe crude product was purified by flash chromatography (SiO2, DCM to DCM/MeOH 9:1)

ORDレコード

ord-77b56e58dd564d26a67018c05b43ba73

出典データセット

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09284331B2