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

HRID 1987516Notes

Reaction equation

HRID 1987516 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].[N+](=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N-].B(F)(F)F>CCOCC>[O:14]=[C:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:13][CH2:12][CH:17]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 12192Ethyl diazoacetateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 44365701-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

tert-Butyl-4-oxo-1-piperidinecarboxylate (10 g, 50.19 mmol) was dissolved in Et2O (100 ml) and cooled to −78° C. Ethyl diazoacetate (7.3 ml, 70.26 mmol) and BF3.EtO were sequentially added over 30 min. After stirring at the same temperature for 2 h, the reaction was quenched by careful addition of aqueous potassium bicarbonate, during which the cold bath was removed. After warming up to room temperature, the organic layer was washed with water, dried over Na2SO4 and concentrated. Purification with flash chromatography provided the titled compound (13 g, Yield: 91%). MS (DCI/NH3) m/z 286 (M+H)+.

Workup

  1. additionEtO were sequentially added over 30 min
  2. customthe reaction was quenched by careful addition of aqueous potassium bicarbonate, during which the cold bath
  3. customwas removed
  4. temperatureAfter warming up to room temperature
  5. washthe organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customPurification with flash chromatography

Sources & evidence

ORD record
ord-ec38fc18c5b84b4f93b96b41a1e0c53a
Source dataset
uspto-grants-2009_06
Patent number
US07550603B2

Reaction notes

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