Reaktionsgleichung
[Na].[CH3:2][C@H:3]([CH2:19][CH2:20][CH3:21])[CH2:4][C:5]([N:7]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][O:9][C:8]1=[O:18])=[O:6].[CH3:22]I>C1COCC1>[CH3:22][C@H:4]([C@H:3]([CH3:2])[CH2:19][CH2:20][CH3:21])[C:5]([N:7]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][O:9][C:8]1=[O:18])=[O:6]Komponenten
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a 1M THF solution of Sodium hexamethyldisylamide (16.2 g, 88.3 mmol) at −78° C. was added via canular a 0° C. solution of (R)-3-((R)-3-methyl-hexanoyl)-4-phenyl-oxazolidin-2-one (18.7 g, 67.9 mmol) in 70 mL dry THF. The resulting solution was stirred at −78° C. for 30 minutes. Methyl Iodide (48.2 g, 339.5 mmol) was added and stirring at −78° C. was continued for 4 hours. The reaction was quenched with saturated ammonium chloride solution, extracted into CH2Cl2 and washed with 1M sodium Bisulfite. The solution was dried over MgSO4, concentrated and chromatographed in 10% ethylacetate in hexane to give the titled compound (11.1 g, 56.5% yield) as an oil. MS, m/z (relative intensity): 1H NMR (400 MHz, CDCl3) δ ppm 0.8 (t, J=7.0 Hz, 3H) 0.9 (d, J=6.6 Hz, 3H) 1.0 (d, J=6.8 Hz, 3H) 1.0 (d, J=8.5 Hz, 1H) 1.1 (m, 1H) 1.4 (m, 1H) 1.7 (m, 1H) 3.7 (m, 1H) 4.2 (dd, J=8.8, 3.4 Hz, 1H) 4.6 (t, J=8.7 Hz, 1H) 5.4 (dd, J=8.7, 3.3 Hz, 1H) 7.2 (m, 2H) 7.3 (m, 3H). MS, m/z (relative intensity):290 [M+1H, 100%].
Aufarbeitung
- stirringstirring at −78° C.
- waitwas continued for 4 hours
- customThe reaction was quenched with saturated ammonium chloride solution
- extractionextracted into CH2Cl2
- washwashed with 1M sodium Bisulfite
- dry with materialThe solution was dried over MgSO4
- concentrationconcentrated
- customchromatographed in 10% ethylacetate in hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-46f2404373214ce589a30c641b43fde6
- Quelldatensatz
- uspto-grants-2008_06
- Patentnummer
- US07388023B2
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