Water → cis-1-(2-benzylphenoxy)-2-(N-methyl-N-tert-butoxycarbonylamino)indane

HRID 965219Notes

Reaction equation

HRID 965219 reaction equation
[H-].[Na+].[CH2:3]([C:10]1[CH:33]=[CH:32][CH:31]=[CH:30][C:11]=1[O:12][C@@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C@@H:14]1[NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH3:35].O>CN(C)C=O>[CH2:3]([C:10]1[CH:33]=[CH:32][CH:31]=[CH:30][C:11]=1[O:12][C@@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C@@H:14]1[N:22]([CH3:35])[C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18661286(+/-)cis-1-(2-Benzylphenoxy)-2-tert-butoxycarbonylaminoindane

Product 1

HCID 18661285cis-1-(2-benzylphenoxy)-2-(N-methyl-N-tert-butoxycarbonylamino)indaneYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (80% disp. in oil, 43 mg, 1.4 mmol) in dry N,N-dimethylformamide (2 ml) under nitrogen was added dropwise a solution of (±)cis-1-(2-benzylphenoxy)-2-tert-butoxycarbonylaminoindane (492 mg, 1.2 mmol) in dimethylformamide (5 ml). After stirring the mixture for 45 minutes at room temperature, iodomethane (88 μl, 1.4 mmol) was added dropwise and stirring continued for a further 45 minutes. The reaction mixture was then poured into a large excess of water and extracted with diethyl ether (3×30 ml). The combined organic extracts were dried over Na2SO4 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 (477 mg).

Workup

  1. stirringstirring
  2. waitcontinued for a further 45 minutes
  3. extractionextracted with diethyl ether (3×30 ml)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e2467d466b745139a2a57fc4439b88b
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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