Hydrochloric Acid → 5-(S)-[5-(tert-Butyl-dimethyl-silanyloxy)-4-cyclopentyl-2-isopropenyl-7,7-dimethyl-5,6,7,8-tetrahydro-quinolin-3-yl]-(4-trifluoromethyl-phenyl)-methanol

HRID 2368640Notes

Reaction equation

[C:1]([Si:5]([CH3:40])([CH3:39])[O:6][C@H:7]1[CH2:16][C:15]([CH3:18])([CH3:17])[CH2:14][C:13]2[N:12]=[C:11]([C:19]([CH3:21])=[CH2:20])[C:10]([C:22]3[C:23]([C:30]([F:33])([F:32])[F:31])=[CH:24][CH:25]=[C:26]([CH:28]=[O:29])[CH:27]=3)=[C:9]([CH:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[C:8]1=2)([CH3:4])([CH3:3])[CH3:2].[H-].[NH4+].[Li].Cl>O1CCCC1.C(OC(=O)C)C>[C:1]([Si:5]([CH3:39])([CH3:40])[O:6][C@H:7]1[CH2:16][C:15]([CH3:18])([CH3:17])[CH2:14][C:13]2[N:12]=[C:11]([C:19]([CH3:21])=[CH2:20])[C:10]([C:22]3[C:23]([C:30]([F:31])([F:32])[F:33])=[CH:24][CH:25]=[C:26]([CH2:28][OH:29])[CH:27]=3)=[C:9]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[C:8]1=2)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

125 mg 5-(S)-[5-(tert-Butyl-dimethyl-silanyloxy)-4-cyclopentyl-2-isopropenyl-7,7-dimethyl-5,6,7,8-tetrahydro-quinolin-3-yl]-(4-trifluoromethyl-phenyl)-methanone are dissolved in 10 ml tetrahydrofurane cooled to 0° C. and mixed with 890 μl of a 1 M solution of lithium ammonium hydride in tetrahydrofurane. The mixture is stirred for 2 h, diluted with ethylacetate and mixed with 890 μl of a 1 M hydrochloric acid. Then the mixture is dried with magnesium sulphate, the solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethylacetate 95:5 to 70:30).

Workup

dry with materialThen the mixture is dried with magnesium sulphate
customthe solvents are evaporated in vacuo
customthe residue is chromatographed on silica gel (cyclohexane/ethylacetate 95:5 to 70:30)

Sources & evidence

ORD record: ord-5dd01627037e46c0bbddc0e6bc00ff47
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703793B2

Reaction notes

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