Sulfuric acid magnesium salt (1:1) → HCID 22640679, compound

HRID 899286Notes

Reaction equation

C([O:3][C:4](=O)[CH:5]([C:11]1[CH:20]=[C:19]2[C:14]([C:15]([CH3:23])([CH3:22])[CH2:16][C:17](=O)[NH:18]2)=[CH:13][CH:12]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O-]S([O-])(=O)=O.[Mg+2]>CCOCC>[CH3:22][C:15]1([CH3:23])[C:14]2[C:19](=[CH:20][C:11]([CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][OH:3])=[CH:12][CH:13]=2)[NH:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-heptanoic acid ethyl ester (3.657 g, 11 mmole) in 100 mL of ether was treated with 1.6 g of lithium aluminum hydride, heated at reflux for four hours and then cooled to 0° C. The reaction mixture was quenched by the successive addition of 1.6 mL water, 1.6 mL 15% sodium hydroxide solution and 4.8 mL water and stirred at room temperature until a white precipitate formed. MgSO4 was added and the mixture was filtered and concentrated in vacuo affording a yellow oil. The product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes) to yield 2.1 g of 2-(4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-heptan-1-ol as a pale yellow oil.

Workup

temperatureheated
temperatureat reflux for four hours
customThe reaction mixture was quenched by the successive addition of 1.6 mL water, 1.6 mL 15% sodium hydroxide solution and 4.8 mL water
customformed
filtrationthe mixture was filtered
concentrationconcentrated in vacuo
customaffording a yellow oil
customThe product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-7324709b12e2401fa127f81e1f2dfc2f
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354931B2

Reaction notes

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