Water → (6S)-8-benzyl-3-chloro-6-methyl-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine

HRID 1877816Notes

Reaction equation

HRID 1877816 reaction equation
[CH2:1]([N:8]([CH2:13][C:14]1[C:19](Cl)=[N:18][C:17]([Cl:21])=[CH:16][N:15]=1)[CH2:9][C@@H:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].O>C1COCC1>[CH2:1]([N:8]1[CH2:13][C:14]2[N:15]=[CH:16][C:17]([Cl:21])=[N:18][C:19]=2[O:12][C@@H:10]([CH3:11])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 86648982HCID 86648982, compound

Product 1

HCID 86648983(6S)-8-benzyl-3-chloro-6-methyl-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepineYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)-1-{benzyl[(3,5-dichloropyrazin-2-yl)methyl]amino}propan-2-ol (3.48 g) in THF (50 mL) was added sodium hydride (513 mg) under ice-cooling, and the mixture was stirred for 2 hr under ice-cooling. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (solvent gradient: 5→20% ethyl acetate/hexane) to give the title compound (1.60 g, 52%) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by basic silica gel column chromatography (solvent gradient: 5→20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c2b29986f8ab4c92946bf1d14c8c6cf0
Source dataset
uspto-grants-2012_11
Patent number
US08314088B2

Reaction notes

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