Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → (RS)-3-(3-Bromo-phenyl)-5-methoxy-3-methyl-3,6-dihydro-2H[1,4]oxazine

HRID 1946904Notes

Reaction equation

HRID 1946904 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.F[B-](F)(F)F.[CH3:21][O+](C)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[N:13]=[C:12]([O:14][CH3:21])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 581553055-(3-Bromophenyl)-5-methylmorpholin-3-one

Product 1

HCID 58155280(RS)-3-(3-Bromo-phenyl)-5-methoxy-3-methyl-3,6-dihydro-2H[1,4]oxazineYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a vacuum dried flask under an argon atmosphere, a solution of (RS)-5-(3-bromo-phenyl)-5-methyl-morpholin-3-one (3.0 g, 11.1 mmol) in dichloromethane (145 ml) was treated with trimethyloxonium tetrafluoroborate (2.594 g, 17 mmol). The reaction mixture was stirred at room temperature for 17 hours. For the workup, the incomplete reaction was extracted with a saturated solution of sodium hydrogen-carbonate (70 ml). The organic layer was dried over sodium sulfate and evaporated. There were obtained 3.12 g of the title compound as light yellow oil containing about 17% of the starting lactam. MS (ISP): m/z=284.2 [M+H]+, 286.1 [M+2+H]+.

Workup

  1. customIn a vacuum dried flask under an argon atmosphere
  2. customFor the workup, the incomplete reaction
  3. extractionwas extracted with a saturated solution of sodium hydrogen-carbonate (70 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-b4cc130aecb043268631b1d56435360b
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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