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

HRID 841879Notes

Reaction equation

HRID 841879 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-3f702c1bdc44406c9c97c78b3aa0d510
Source dataset
uspto-grants-2002_04
Patent number
US06372733B1

Reaction notes

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