Sodium borohydride → (2S,5S)-1-tert-butyl 2-ethyl 5-hydroxypiperidine-1,2-dicarboxylate
Reaktionsgleichung
[BH4-].[Na+].[O:3]=[C:4]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:6][CH2:5]1>CCO>[OH:3][C@@H:4]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C@H:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:6][CH2:5]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -40 °C
Versuchsvorschrift
NaBH4 (36 g, 1.0 mol) was added in portions to a −40° C. solution of (S)-1-tert-butyl 2-ethyl 5-oxopiperidine-1,2-dicarboxylate (250 g, 0.92 mol) in EtOH (1500 mL). The reaction mixture was then stirred at −40° C. for 0.5 hr then quenched with 10% HOAc solution. After diluting with water, the mixture was extracted with DCM (3×). The combined organic layer was concentrated under reduced pressure and purified by silica gel column chromatography (1:1 petroleum ether/EtOAc) to afford (2S,5S)-1-tert-butyl 2-ethyl 5-hydroxypiperidine-1,2-dicarboxylate (205 g, 80%) as a yellow oil.
Aufarbeitung
- customthen quenched with 10% HOAc solution
- additionAfter diluting with water
- extractionthe mixture was extracted with DCM (3×)
- concentrationThe combined organic layer was concentrated under reduced pressure
- custompurified by silica gel column chromatography (1:1 petroleum ether/EtOAc)
Quellen und Nachweise
- ORD-Eintrag
- ord-959ceb2592da4ee5b3b173d8d3e740df
- Quelldatensatz
- uspto-grants-2015_01
- Patentnummer
- US08927724B2
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