Reaktionsgleichung
C([O:8][C:9](=O)[CH2:10][C@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][O:13][CH3:14])C1C=CC=CC=1.[Li+].[BH4-].C1COCC1>C(OCC)C>[C:19]([O:18][C:16](=[O:17])[NH:15][C@H:11]([CH2:12][O:13][CH3:14])[CH2:10][CH2:9][OH:8])([CH3:22])([CH3:21])[CH3:20]Komponenten
5
Versuchsvorschrift
A solution of (S)-3-tert-Butoxycarbonylamino-4-methoxy-butyric acid benzyl ester (10.4 g, 32.3 mmol) in dry diethylether (70 ml) cooled to 0° C. is treated slowly with a 2.0 M solution of LiBH4 in THF (32.2 ml, 64.4 mmol). The reaction mixture is allowed to warm to ambient temperature and then left to stir. After 6 hours the reaction mixture is quenched slowly with 0.5 M aqueous solution of citric acid and extracted with ether. The ether phase is dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (elution with a gradient 3:7 to 6:4 ethylacetate/hexane) to afford ((S)-3-Hydroxy-1-methoxymethyl-propyl)-carbamic acid tert-butyl ester as a clear oil. [M-BOC] 120.13
Aufarbeitung
- waitleft
- customAfter 6 hours the reaction mixture is quenched slowly with 0.5 M aqueous solution of citric acid
- extractionextracted with ether
- dry with materialThe ether phase is dried over magnesium sulphate
- customevaporated
- customThe crude product is purified by flash silica chromatography (
- washelution with a gradient 3:7 to 6:4 ethylacetate/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-21cdab5396d74da699493784cc7af339
- Quelldatensatz
- uspto-grants-2007_10
- Patentnummer
- US07288537B2
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