HCID 14143058, Verbindung → (S)-4-Benzyl-3-methylmorpholine
Reaktionsgleichung
[CH3:1][C@@H:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=O)[CH2:5][O:4][CH2:3]1.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH3:1][C@H:2]1[CH2:3][O:4][CH2:5][CH2:6][N:7]1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a 0° C. solution of (5S)-5-methyl-4-(phenylmethyl)-3-morpholinone (12.74 g, 62.07 mmol) in toluene (150 mL) was added Red-Al (65% w/w in PhMe, 38 mL) dropwise via addition funnel. The resulting solution was heated at 60° C. and stirred for 4 h, then cooled to 40° C. and stirred overnight. The solution was then cooled to 0° C. and quenched by dropwise addition of 1 N aq. NaOH (15 mL). The mixture was diluted with Et2O (100 mL) and washed with 1 N aq. NaOH (100 mL) followed by brine (50 mL). The organic phase was dried over anhydrous Na2SO4, filtered, concentrated in vacuo, and azeotroped with MeOH (50 mL) to provide (3S)-3-methyl-4-(phenylmethyl)morpholine (11.33 g, 95%) as a faintly pink oil. LCMS: (M+H)+: 192.2.