Methyl iodide → HCID 53822127, compound

HRID 343918Notes

Reaction equation

HRID 343918 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@@H:9]1[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].I[CH3:30].[Cl-].[NH4+]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@@H:9]1[N:17]([CH3:30])[C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 53788645HCID 53788645, compound

Product 1

HCID 53822127HCID 53822127, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (80% disp. in oil, 130 mg, 4.2 mmol) in dry N,N-dimethylformamide (6 ml) under nitrogen was added dropwise a solution of (±) cis-1-(3,4-dichlorobenzyl)-2-tert-butoxycarbonylaminoindane (1.65 g, 4.2 mmol) in N, N-dimethylformamide (10 ml). After stirring the mixture for 30 minutes at room temperature, iodomethane (0.28 ml, 4.5 mmol) was added dropwise and stirring continued for a further 1 h. The reaction mixture was then poured into a large excess of sat. ammonium chloride and extracted with diethyl ether (3×40 ml). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. The residue was subjected to column chromatography on silica gel eluting with 10% diethyl ether in hexanes to afford the title compound as a colourless oil (1.02 g).

Workup

  1. stirringstirring
  2. waitcontinued for a further 1 h
  3. extractionextracted with diethyl ether (3×40 ml)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be8097ee34f14f4f8d55ba5f5fa51a9a
Source dataset
uspto-grants-1999_01
Patent number
US05863952

Reaction notes

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