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

HRID 1159089Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-9cde38c6b72548c5b9423c2011e50b47
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812024B2

Reaction notes

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