Methyl iodide → HCID 66684293, Verbindung

Temperatur

-78 °C

To a solution of diisopropyl amine (138 mg, 1.36 mmol, 1.3 equiv) in THF (6.0 mL) at −78° C. was added n-BuLi (0.79 mL, 1.6 mL in heptane, 1.26 mmol, 1.2 equiv) and the resulting solution was stirred at −78° C. for 10 minutes. To the solution was added a solution of 2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-5-cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-one (500 mg, 1.05 mmol, 1.0 equiv) in THF (2 mL) and the solution was stirred at −78° C. for 30 mins. MeI was added and the solution was stirred at −78° C. for 1 hour then slowly warmed to room temperature over 2 hours. The reaction was quenched by addition of sat. aq. NH4Cl solution. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography, EtOAc/heptane 20% to give product (S)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-5-cyclohexyl-4-(4-methoxy-benzyl)-2-methyl-morpholin-3-one 110 mg and product (R)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-5-cyclohexyl-4-(4-methoxy-benzyl)-2-methyl-morpholin-3-one 205 mg.

1. stirringthe solution was stirred at −78° C. for 30 mins
2. stirringthe solution was stirred at −78° C. for 1 hour
3. temperaturethen slowly warmed to room temperature over 2 hours
4. customThe reaction was quenched by addition of sat. aq. NH4Cl solution
5. extractionThe mixture was extracted with EtOAc
6. washThe organic layer was washed with brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customThe residue was purified by silica gel column chromatography, EtOAc/heptane 20%

ORD-Eintrag

ord-f7c5c5b36d8b42729af3228d14c03a48

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09040690B2