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

HRID 239167Notes

Reaction equation

HRID 239167 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-e991e46d97ec47fea975d216eb296f6b
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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