Ethyl Acetate → HCID 58076885, compound

HRID 400478Notes

Reaction equation

HRID 400478 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[N:12]1([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:18][CH2:17][CH:16]=[CH:15][CH2:14][CH2:13]1.C(OCC)(=O)C>ClCCl>[CH:16]12[O:9][CH:15]1[CH2:14][CH2:13][N:12]([C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[CH2:18][CH2:17]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 45043132Benzyl 2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

Product 1

HCID 58076885HCID 58076885, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

18 g m-chloroperbenzoic acid was added to 10 g benzyl 2,3,6,7-tetrahydro-1H-azepine-1-carboxylate in 250 ml dichloromethane at 0° C. in several portions. The mixture was allowed to warm to RT over 2 h. 1 L ethyl acetate was added and the solution was extracted with aqueous sodium bicarbonate, 1N aqueous sodium hydroxide and brine. The organic layer was evaporated and the residue was purified by chromatographie on silica gel (ethyl acetae/hexanes 1:5) to yield 10.4 g of the desired product.

Workup

  1. extractionthe solution was extracted with aqueous sodium bicarbonate, 1N aqueous sodium hydroxide and brine
  2. customThe organic layer was evaporated
  3. customthe residue was purified by chromatographie on silica gel (ethyl acetae/hexanes 1:5)

Sources & evidence

ORD record
ord-fecb9bad3bba4fbfbc041099ef57846c
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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