Sodium t-butoxide → (7RS)-7-(3,4-dichlorophenyl)-7-(methoxymethyl)-1,4-oxazepan-3-one

HRID 1022581Notes

Reaction equation

HRID 1022581 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH2:7][C:8]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)([OH:12])[CH2:9][O:10][CH3:11])=[O:4].CC(C)([O-])C.[Na+]>C1COCC1>[Cl:20][C:15]1[CH:14]=[C:13]([C:8]2([CH2:9][O:10][CH3:11])[O:12][CH2:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7]2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

4

Reactant 2

HCID 23676156Sodium t-butoxideHCID 669764072-chloro-N-[(3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-methoxybutyl]acetamide

Product 1

HCID 66975909(7RS)-7-(3,4-dichlorophenyl)-7-(methoxymethyl)-1,4-oxazepan-3-oneYield 113.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-N-[(3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-methoxybutyl]acetamide (2.10 g) in THF (150 ml) was added sodium tert-butoxide (592 mg), and the mixture was heated under reflux for 10 min. The reaction mixture was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (1:1)-ethyl acetate:methanol (4:1)) to give the title compound (2.13 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 min
  3. customThe reaction mixture was quenched with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (1:1)-ethyl acetate:methanol (4:1))

Sources & evidence

ORD record
ord-6b561301de4341a083e53bfaf30552a8
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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