Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 22617758, compound

HRID 1638134Notes

Reaction equation

HRID 1638134 reaction equation
F[B-](F)(F)F.[CH3:6][O+](C)C.[C:10]([O:14][C:15]([N:17]1[CH2:23][CH2:22][C:21](=[O:24])[NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>C(Cl)Cl>[C:10]([O:14][C:15]([N:17]1[CH2:23][CH2:22][C:21]([O:24][CH3:6])=[N:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 226177365-Oxo-(1,4)diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 22617758HCID 22617758, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethyloxonium tetrafluoroborate (Meerwein's salt) (141 mg, 0.94 mmol) was added in one portion to a solution of 1-(tert-butoxycarbonyl)hexahydro-(5H)-1,4-diazepin-5-one (200 mg, 0.94 mmol) in 2.0 mL of anhydrous methylene chloride. The mixture was stirred overnight at room temperature. The reaction mixture was partitioned between 10 mL of saturated aqueous sodium bicarbonate and 20 mL of ethyl acetate. The organic layer was separated and the aqueous layer was extracted with 3×10 mL of ethyl acetate. The combined ethyl acetate layers were washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the organic solution was concentrated in vacuo to give 180 mg (85%) of 1-(tert-butoxycarbonyl)-2,3,6,7-tetrahydro-5-methoxy-(1H)-1,4-diazepine as a yellow liquid.

Workup

  1. customThe reaction mixture was partitioned between 10 mL of saturated aqueous sodium bicarbonate and 20 mL of ethyl acetate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 3×10 mL of ethyl acetate
  4. washThe combined ethyl acetate layers were washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. concentrationthe organic solution was concentrated in vacuo

Sources & evidence

ORD record
ord-ee9d90b89cb743028ec0148c55021e19
Source dataset
uspto-grants-2000_03
Patent number
US06043358

Reaction notes

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