HCID 66763075, compound → HCID 66762949, compound

HRID 573799Notes

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](=[O:23])[CH3:22])[C:12]3[C@@H:24]([C:32]4[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=4)[O:25][C:26]4([CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[C:11]=3[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:42][Mg]Br>O1CCCC1.C1(C)C=CC=CC=1.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]([C:21]([OH:23])([CH3:42])[CH3:22])[C:12]3[C@@H:24]([C:32]4[CH:33]=[CH:34][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:36][CH:37]=4)[O:25][C:26]4([CH2:31][CH2:30][O:29][CH2:28][CH2:27]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

26 mg 1-((3R,9S)-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-yl)ethanone are dissolved in 2 ml tetrahydrofurane cooled to −10° C. and treated with 110 μl of a 1.4 M solution of methylmagnesium bromide in toluene/tetrahydrofurane 75:25. The mixture is warmed to room temperature and stirred for 12 hours. The mixture is diluted with diethylether, washed with saturated aqueous ammonium chloride and dried with magnesium sulphate. The solvents are evaporated in vacuo and the residue is directly used in the next step.

Workup

temperatureThe mixture is warmed to room temperature
washwashed with saturated aqueous ammonium chloride
dry with materialdried with magnesium sulphate
customThe solvents are evaporated in vacuo

Sources & evidence

ORD record: ord-08c0cd523a1c4e399ab1df912a36debd
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029544B2

Reaction notes

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