Methanol → HCID 58938541, compound

HRID 598108Notes

Reaction equation

[CH2:1]([N:4]([CH2:8][C:9]1[CH:10]=[C:11]([C:29](OCC)=[O:30])[C:12](=[O:28])[N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]1[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=1[CH3:27])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[H-].C([Al+]CC(C)C)C(C)C.CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[CH2:1]([N:4]([CH2:8][C:9]1[CH:10]=[C:11]([CH2:29][OH:30])[C:12](=[O:28])[N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]1[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=1[CH3:27])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

Conditions

Temperature: -40 °C

Procedure

Ethyl 1-((dipropylamino)methyl)-6-mesityl-4-oxo-4H-quinolizine-3-carboxylate (0.228 g, 0.51 mmol) was dissolved in tetrahydrofuran (3.5 mL). The solution was cooled to −40° C. and diisobutylaluminum hydride (DIBAL-H) (1M, 1.5 mL, 1.5 mmol) was added rapidly. The reaction stirred for 1 h and was warmed to room temperature. Methanol and Rochelle's salt were added and the mixture stirred at room temperature for 3 h. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried, concentrated, and flash chromatographed (2% methanol/ethyl acetate) to give 0.096 g (46% yield) of the desired product.

Workup

temperaturewas warmed to room temperature
stirringthe mixture stirred at room temperature for 3 h
customThe organic layer was separated
extractionthe aqueous layer was extracted with dichloromethane
customThe combined organic layers were dried
concentrationconcentrated
customflash chromatographed (2% methanol/ethyl acetate)

Sources & evidence

ORD record: ord-17ff2bb1ee834aee8620022eb64f1bd9
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

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