Methyl iodide → (S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-yl(methyl)carbamate

HRID 529558Notes

Reaction equation

HRID 529558 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]1=[O:24].[H-].[Na+].I[CH3:28]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]([N:16]([CH3:28])[C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[C:10]1=[O:24]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68310539(S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamate

Product 1

HCID 68310944(S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-yl(methyl)carbamateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

THF (0.8 mL) was added to a reaction vessel containing (S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamate (53 mg, 0.16 mmol). NaH (60% dispersion in oil, 25.4 mg, 0.634 mmol) was then added to the reaction mixture followed by iodomethane (180 mg, 1.27 mmol). The turbid mixture was left to stir at rt for 2 hr. The reaction was quenched by addition of water. The mixture was concentrated to remove some of the THF. The mixture was then partitioned between EtOAc and water. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give (S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-yl(methyl)carbamate (52 mg, 0.15 mmol, 94% yield) as a colorless oil.

Workup

  1. waitThe turbid mixture was left
  2. customThe reaction was quenched by addition of water
  3. concentrationThe mixture was concentrated
  4. customto remove some of the THF
  5. customThe mixture was then partitioned between EtOAc and water
  6. customThe organic phase was isolated
  7. washwashed with saturated aqueous NaCl
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9373840662834fe39547364611ad16b7
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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