Water → (+)-2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-hydroxyethyl)quinoline

HRID 1167184Notes

Reaction equation

[C:1]1([C:7]2[C:16]([CH3:17])=[CH:15][C:14]3[C:9](=[C:10]([C@@H:18]([N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]4[CH3:34])[CH2:19][O:20][Si](C(C)(C)C)(C)C)[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.O.C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)C>[C:1]1([C:7]2[C:16]([CH3:17])=[CH:15][C:14]3[C:9](=[C:10]([C@@H:18]([N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]4[CH3:34])[CH2:19][OH:20])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 0.5 g (1.05 mmol) of 2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-[tert-butyldimethylsilyloxy]ethyl)quinoline in a mixture of 15 ml of acetic acid, 5 ml of tetrahydrofuran and 5 ml of distilled water is heated at 70° C. for 40 hours and is then poured onto an ice-cold mixture of 150 ml of ethyl ether and of 150 ml of a saturated sodium hydrogencarbonate solution. The addition of sodium hydrogencarbonate is continued until a pH of approximately 9 is obtained. The mixture is then extracted with 3×200 ml of ethyl ether. The organic phases are combined, dried over magnesium sulfate, filtered and evaporated under vacuum. The residue is purified by silica gel chromatography (eluent: dichloromethane/methanol 9/1) to provide 0.3 g of (+)-2-phenyl-3-methyl-8-(1-(R)-[2-(R)-methylpiperidino]-2-hydroxyethyl)quinoline in the form of a colorless wax. (Yield: 75%)

Workup

customis obtained
extractionThe mixture is then extracted with 3×200 ml of ethyl ether
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated under vacuum
customThe residue is purified by silica gel chromatography (eluent: dichloromethane/methanol 9/1)

Sources & evidence

ORD record: ord-5f31a7c07bd942a0b91df72c8ed2f3dc
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617336B1

Reaction notes

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