Methyl iodide → HCID 66918501, compound

HRID 1367476Notes

Reaction equation

HRID 1367476 reaction equation
[C:1]([Si:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][C@@H:7]1[CH2:11][C@H:10]([C:12]#[N:13])[C@@H:9]([OH:14])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH3:27]I>[Ag-]=O>[C:1]([Si:5]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][C@@H:7]1[CH2:11][C@H:10]([C:12]#[N:13])[C@@H:9]([O:14][CH3:27])[CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 66918517HCID 66918517, compound

Product 1

HCID 66918501HCID 66918501, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 178418778HCID 178418778, compoundCatalyst

Procedure

A mixture of (1S,2R,4S) and (1R,2S,4R)-4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-cyclopentanecarbonitrile (2 g, 5.47 mmol), methyliodide (15 ml; 246 mmol) and silver(I) oxide (2.54 g, 10.94 mmol) was stirred at room temperature overnight. The excess of methyliodide was removed under reduced pressure and the remaining residue was suspended in DCM and filtered through a pad of celite. The filtrate was evaporated and the remaining yellow gum was purified by silica gel column chromatography (heptane/EtOAc 90:10-80:20) to obtain 1.62 g (4 mmol, 78%) of the title compound as colorless gum. MS (EI): 380.2 (M+H)+.

Workup

  1. customThe excess of methyliodide was removed under reduced pressure
  2. filtrationfiltered through a pad of celite
  3. customThe filtrate was evaporated
  4. customthe remaining yellow gum was purified by silica gel column chromatography (heptane/EtOAc 90:10-80:20)

Sources & evidence

ORD record
ord-3470dedc7f064772ae8adf0071cd8446
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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