Sodium cyanoborohydride → O-methyl-N-[1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethyl]-hydroxylamine
Reaktionsgleichung
[CH3:1][O:2][N:3]=[C:4]([CH:6]1[CH2:11][CH2:10][C:9]([CH3:12])=[CH:8][C:7]1([CH3:14])[CH3:13])[CH3:5].C([BH3-])#N.[Na+]>C(O)(=O)C.[OH-].[Na+].O>[CH3:1][O:2][NH:3][CH:4]([CH:6]1[CH2:11][CH2:10][C:9]([CH3:12])=[CH:8][C:7]1([CH3:13])[CH3:14])[CH3:5]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 24 °C
Versuchsvorschrift
To a stirred solution of 1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethanone O-methyl-oxime (135 g; 0.69 mol), prepared as described in example P5, in acetic acid (650 ml) was added portionwise sodium cyanoborohydride (67 g; 1.04 mol). The reaction mixture was stirred at 24° C. for 16 hours under nitrogen atmosphere. Most of acetic acid was removed under reduced pressure. The yellow sticky oil obtained was poured in 2M sodium hydroxide (800 ml) and water (100 ml). The solution was extracted with dichloromethane (3×300 ml). Combined organic layers were washed with sodium bicarbonate (500 ml) and dried over sodium sulfate. The solvent was removed in vacuo to afford 128 g (94% of theory) of O-methyl-N-[1-(2,2,4-trimethyl-cyclohex-3-enyl)-ethyl]-hydroxylamine (mixture of two diastereomers) as a cloudy yellow oil.
Aufarbeitung
- customMost of acetic acid was removed under reduced pressure
- customThe yellow sticky oil obtained
- extractionThe solution was extracted with dichloromethane (3×300 ml)
- washCombined organic layers were washed with sodium bicarbonate (500 ml)
- dry with materialdried over sodium sulfate
- customThe solvent was removed in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-0c9539ecafac44a9a8d4f37b39fedef4
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08536215B2
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