Boron trifluoride etherate → Diethyl 5-oxoazepane-1,4-dicarboxylate

HRID 2237438Notes

Reaction equation

HRID 2237438 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].B(F)(F)F.O(CC)CC.[N+](=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N-]>CCOCC>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][C:9](=[O:12])[CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12192Ethyl diazoacetateHCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

Product 1

HCID 12485293Diethyl 5-oxoazepane-1,4-dicarboxylateYield 101%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-30 °C

Procedure

4-Oxo-piperidine-1-carboxylic acid ethyl ester (20 g, 117 mmol) was dissolved in 120 mL Et2O and cooled to −30° C. BF3-OEt2 (14.8 mL) and ethyl diazoacetate (16 mL, 152 mmol) were added simultaneously (each in 15 mL Et2O) over the course of 30 minutes, maintaining an internal temperature of approximately −20° C. The reaction was warmed to room temperature and stirred for 3 hours after which time the reaction was quenched carefully with 30% K2CO3 (60 mL). The organic layer was dried over K2CO3 and concentrated to give 30.4 g of the subtitle compound.

Workup

  1. temperaturemaintaining an internal temperature of approximately −20° C
  2. temperatureThe reaction was warmed to room temperature
  3. customwas quenched carefully with 30% K2CO3 (60 mL)
  4. dry with materialThe organic layer was dried over K2CO3
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d7164c6dbda04f4a8cd1de872791c404
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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