Ethyl Acetate → HCID 58076885, compound

HRID 239175Notes

Reaction equation

HRID 239175 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 acetate/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 acetate/hexanes 1:5)

Sources & evidence

ORD record
ord-f4cb53933cea4d9da29a75896b0cf7e1
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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