Dimethylformamide → HCID 86656347, compound

HRID 1942464Notes

Reaction equation

HRID 1942464 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([C:17]([N:19]([CH:33]([CH3:35])[CH3:34])[C@@H:20]3[CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]3)=[O:18])[C:14]([CH3:16])=[CH:15][C:10]=2[O:9][C:8]([CH3:37])([CH3:36])[C:7]1=[O:38].[H-].[Na+].CN(C)C=O.Br[CH:47]1[CH2:49][CH2:48]1>O>[CH:47]1([O:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:11]3[CH:12]=[C:13]([C:17]([N:19]([CH:33]([CH3:34])[CH3:35])[C@@H:20]4[CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:21]4)=[O:18])[C:14]([CH3:16])=[CH:15][C:10]=3[O:9][C:8]([CH3:36])([CH3:37])[C:7]2=[O:38])[CH2:49][CH2:48]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 78037BromocyclopropaneHCID 67332567HCID 67332567, compound

Product 1

HCID 86656347HCID 86656347, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To tert-butyl (3R)-3-[{[4-(4-hydroxybutyl)-2,2,7-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (200 mg) were added sodium hydride (60 mg) and N,N-dimethylformamide (3 ml) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. Then, to the mixture was added bromocyclopropane (0.30 ml), and the mixture was stirred at 150° C. for 6 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate solution. The obtained ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to give the title compound (30 mg) as a colorless liquid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 150° C. for 6 hours
  3. extractionthe mixture was extracted with ethyl acetate solution
  4. washThe obtained ethyl acetate solution was washed with water
  5. dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-e109db7d0318444fb9aaa0f05aeaad99
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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