Aluminium lithium hydride → (S)-tert-butyl 5-(hydroxymethyl)-6-azaspiro[2.5]octane-6-carboxylate
Reaktionsgleichung
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([CH2:13][CH2:12]2)[CH2:10][C@H:9]1[C:16](OCC1C=CC=CC=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:11]2([CH2:13][CH2:12]2)[CH2:10][C@H:9]1[CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Alternatively Intermediate 18 was prepared from Intermediate 16. To a suspension of lithium aluminium hydride (0.57 g, 15 mmol) in anhydrous THF (30 ml) was added the solution of (S)-6-aza-spiro[2.5]octane-5,6-dicarboxylic acid 5-benzyl ester 6-tert-butyl ester (intermediate 16, 3.45 g, 10 mmol) in THF(20 ml) at 0° C., after the addition was completed, the reaction mixture was stirred at 0° C. for 2 hours. The resulting mixture was quenched with Na2SO4.10H2O, filtered and the filtration was dried (Na2SO4) and evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether/ethyl acetate from 10/1 to 5/1). (S)-5-Hydroxymethyl-6-aza-spiro[2.5]octane-6-carboxylic acid tert-butyl ester was obtained as colourless oil (2.0 g), yield:83%.
Aufarbeitung
- additionafter the addition
- customThe resulting mixture was quenched with Na2SO4.10H2O
- filtrationfiltered
- filtrationthe filtration
- dry with materialwas dried (Na2SO4)
- customevaporated
- customto obtain a crude that
- customwas purified by silica gel chromatography (petroleum ether/ethyl acetate from 10/1 to 5/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-aed63fa427914470b635e1519ae1ce41
- Quelldatensatz
- uspto-grants-2014_10
- Patentnummer
- US08859608B2
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