Dimethylformamide → HCID 86707861, compound

HRID 922436Notes

Reaction equation

HRID 922436 reaction equation
[CH:1]1([N:4]([CH:12]([C:14]2[CH:23]=[C:22]([OH:24])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH3:13])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.[C:25](=O)([O-])[O-].[K+].[K+].CN(C)C=O.CI>O>[CH:1]1([N:4]([CH:12]([C:14]2[CH:23]=[C:22]([O:24][CH3:25])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH3:13])[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68309708HCID 68309708, compound

Product 1

HCID 86707861HCID 86707861, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of tert-butyl cyclopropyl[1-(4-hydroxy2-naphthyl)ethyl]carbamate (43 mg) and potassium carbonate (27 mg) was added N,N-dimethylformamide (2.0 mL), and then thereto added methyl iodide (0.016 mL), and the mixture was stirred at room temperature for 4 hours. After cooling, to the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water twice and saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1→4/1) to give tert-butyl cyclopropyl[1-(4-methoxy-2-naphthyl)ethyl]carbamate [REx(4-1)] (33 mg) as a colorless oil.

Workup

  1. temperatureAfter cooling, to the reaction solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was sequentially washed with water twice
  4. dry with materialsaturated saline, dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1→4/1)

Sources & evidence

ORD record
ord-b88d5eda34e34a9b835f330c888e9800
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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