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

HRID 400470Notes

Reaction equation

HRID 400470 reaction equation
B(F)(F)F.CCOCC.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[CH2:24]([O:26][C:27](=[O:31])[CH:28]=[N+]=[N-])[CH3:25]>C(OCC)C>[CH2:24]([O:26][C:27]([CH:28]1[C:20](=[O:23])[CH2:19][CH2:18][N:17]([C:15]([O:14][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:16])[CH2:22][CH2:21]1)=[O:31])[CH3:25]

Participants

5

Reactant 3

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

Product 1

HCID 44365701-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylateYield 52.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3 mL boron trifluoride etherate was added to 4 g 4-oxo-piperidine-1-carboxylic acid tert-butyl ester in 30 mL diethyl ether at −30° C. Then 3.5 g diazo-acetic acid ethyl ester in diethyl ether was added at the same temperature and stirred for 30 min. The reaction was poured in to ice water and the organic layer was separated, washed with aqueous sodiumcarbonate solution, dried and evaporated to give 3 g of the desired product.

Workup

  1. customthe organic layer was separated
  2. washwashed with aqueous sodiumcarbonate solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-44a7f0fe946242548895639bf730ac23
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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