Methyl iodide → HCID 15888165, compound

HRID 342106Notes

Reaction equation

HRID 342106 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C@@H:10]3[CH2:12][C@H:11]3[CH2:13][NH:14][C:15](=[O:18])[CH2:16][CH3:17])[C:4]=2[CH2:3][CH2:2]1.[H-].[Na+].I[CH3:22]>C1COCC1>[CH3:22][N:14]([CH2:13][C@@H:11]1[CH2:12][C@H:10]1[C:9]1[C:4]2[CH2:3][CH2:2][O:1][C:5]=2[CH:6]=[CH:7][CH:8]=1)[C:15](=[O:18])[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10220503Tasimelteon

Product 1

HCID 15888165HCID 15888165, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl]methyl]propanamide (120 mg, 0.6 mmol) in THF (1.5 mL) was added sodium hydride (30 mg of 60%, 0.75 mmol). The mixture was allowed to stir for 0.5 h and iodomethane (140 mg, 1 mmol) was added. After stirring for 18 h, the solution was concentrated in vacuo. The residue was dissolved in acetonitrile and washed with hexane. The acetonitrile solution was concentrated in vacuo and the residue purified by chromatography on silica eluting with ethyl acetate-hexane (2:8) to give the product as an amber oil (90 mg, 69%). Anal. Calc'd for C16H21NO2. 0.2H2O: C, 73.08; H, 8.20; N 5.33; Found: C, 72.91; H, 8.24; N, 5.23.

Workup

  1. stirringAfter stirring for 18 h
  2. concentrationthe solution was concentrated in vacuo
  3. dissolutionThe residue was dissolved in acetonitrile
  4. washwashed with hexane
  5. concentrationThe acetonitrile solution was concentrated in vacuo
  6. customthe residue purified by chromatography on silica eluting with ethyl acetate-hexane (2:8)

Sources & evidence

ORD record
ord-87e3e82feaae4df68d479ccb8174773f
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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