Methyl iodide → HCID 66761672, compound

HRID 573798Notes

Reaction equation

HRID 573798 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]([OH:24])([CH3:23])[CH3:22])[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-].[Na+].[CH3:45]I>CN(C)C=O.C(OCC)C>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][C:15]2[N:14]=[C:13]([C:21]([O:24][CH3:45])([CH3:23])[CH3:22])[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

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66762949HCID 66762949, compound

Product 1

HCID 66761672HCID 66761672, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

25 mg 2-((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)propan-2-ol are dissolved in 1 ml N,N-dimethylformamide, cooled to 0° C., treated with 3 mg sodium hydride (60% in mineral oil) and stirred for 1 minute. Then 5 μl methyliodide are added and the mixture is stirred for 4 hours at room temperature. The mixture is diluted with diethylether, washed with saturated aqueous ammonium chloride and dried with magnesium sulphate.

Workup

  1. stirringthe mixture is stirred for 4 hours at room temperature
  2. washwashed with saturated aqueous ammonium chloride
  3. dry with materialdried with magnesium sulphate

Sources & evidence

ORD record
ord-7561b71e913d47e0853c3f6491e6e0eb
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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