Hydrochloric Acid → HCID 66763041, compound

HRID 573797Notes

Reaction equation

[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([C:21](OC)=[O:22])[C:12]3[C@@H:25]([C:33]4[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=4)[O:26][C:27]4([CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[C:11]=3[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1.C(OCC)C>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH2:21][OH:22])[C:12]3[C@@H:25]([C:33]4[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:40])[F:41])=[CH:35][CH:34]=4)[O:26][C:27]4([CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[C:11]=3[C:10]1=2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -10 °C

Procedure

1.28 g (3R,9S)-methyl 9-(tert-butyldimethylsilyloxy)-7,7-dimethyl-3-(4-(trifluoromethyl)phenyl)-2′,3′,5′,6,6′,7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran]-4-carboxylate are dissolved in 10 ml tetrahydrofurane cooled to −10° C. and treated dropwise with 1.2 ml of a 1 M solution of lithiumaluminium hydride in tetrahydrofurane. The mixture is warmed to room temperature and stirred for 1 hour. Then it is diluted with diethylether and treated under vigorous stirring with 1 M hydrochloric acid. The organic phase is separated, dried with magnesium sulphate and evaporated in vacuo. The residue is chromatographed on silica gel (petrole ether/ethylacetate 70:30 to 40:60).

Workup

temperatureThe mixture is warmed to room temperature
additiontreated
customThe organic phase is separated
dry with materialdried with magnesium sulphate
customevaporated in vacuo
customThe residue is chromatographed on silica gel (petrole ether/ethylacetate 70:30 to 40:60)

Sources & evidence

ORD record: ord-064559645b02453bafa579014212009d
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029544B2

Reaction notes

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