Aluminium lithium hydride → (R)-Tert-butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Reaktionsgleichung

[H-].[Al+3].[Li+].[H-].[H-].[H-].CON(C)[C:10]([C@H:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][N:13]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:11]>CCOCC>[CH:10]([C@H:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][N:13]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:11]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Lithium aluminum hydride (1 M in THF, 5.3 ml, 5.3 mmol) was added to a solution of (3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1.7 g, 5.0 mmol theory) in ether (16 ml) stirring at 0° C. under nitrogen. After stirring at 0° C. for 1 h, the reaction was slowly quenched with water (0.40 ml). Sodium hydroxide (1N, 0.80 ml) followed by water (0.60 ml) were then added and the resultant gelatinous precipitate was filtered through Celite® rinsing with ether and THF. The filtrate was evaporated and the residue transferred to a separatory funnel with EtOAc. Washing with brine and drying with MgSO4 afforded crude product (1.3 g, 100% yield) which was used in the next step without further purification.

Aufarbeitung

stirringAfter stirring at 0° C. for 1 h
customthe reaction was slowly quenched with water (0.40 ml)
additionwere then added
filtrationthe resultant gelatinous precipitate was filtered through Celite®
washrinsing with ether and THF
customThe filtrate was evaporated
customthe residue transferred to a separatory funnel with EtOAc
washWashing with brine
dry with materialdrying with MgSO4

Quellen und Nachweise

ORD-Eintrag: ord-b010bec74e674166822b3bdacb347dbc
Quelldatensatz: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07244843B2

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