Boron trifluoride etherate → 1-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate

HRID 528707Notes

Reaction equation

HRID 528707 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B(F)(F)F.CCOCC.[N+](=[CH:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N-].C(=O)([O-])[O-].[K+].[K+]>CCOCC>[CH2:30]([O:29][C:27]([CH:26]1[C:11](=[O:14])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:13][CH2:12]1)=[O:28])[CH3:31]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 12192Ethyl diazoacetateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 44365701-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To 10.0 g (50.18 mmol) 4-oxo-piperidine-1-carboxylic acid tert-butyl ester in 60 mL anhydrous ether maintained between −25° C. and −30° C. were added, over 20 minutes, solutions of 8.2 mL (65.23 mmol) boron trifluoride diethyl etherate in 17 mL anhydrous ether, followed by 6.85 mL (65.23 mmol) ethyl diazoacetate in 17 mL anhydrous ether, and the reaction was maintained between −25° C. and −30° C. for 1 hour. The mixture was allowed to warm to room temperature, 30 mL 30% potassium carbonate solution was added and the mixture extracted with EtOAc (3×30 mL), the organic layers were combined and dried with MgSO4. After filtration, the solvent was evaporated to give the desired product.

Workup

  1. additionwere added, over 20 minutes
  2. temperaturethe reaction was maintained between −25° C. and −30° C. for 1 hour
  3. extractionthe mixture extracted with EtOAc (3×30 mL)
  4. dry with materialdried with MgSO4
  5. filtrationAfter filtration
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-20eb548a9b5b4a9298944ceafbfd18e6
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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