Water → HCID 86612714, compound

HRID 553966Notes

Reaction equation

HRID 553966 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]1[CH:14]=[C:15]([C@@H:21]2[CH:30]=[CH:29][CH2:28][C@@H:27]3[N:22]2[C:23](=[O:31])[CH2:24][CH2:25][CH2:26]3)[CH:16]=[C:17]([F:20])[C:18]=1[F:19].O.C(OCC)(=[O:35])C>C(Cl)Cl>[F:20][C:17]1[CH:16]=[C:15]([C@H:21]2[N:22]3[C@H:27]([CH2:26][CH2:25][CH2:24][C:23]3=[O:31])[CH2:28][C@@H:29]3[O:9][C@H:30]23)[CH:14]=[C:13]([F:12])[C:18]=1[F:19].[F:20][C:17]1[CH:16]=[C:15]([C@H:21]2[N:22]3[C@H:27]([CH2:26][CH2:25][CH2:24][C:23]3=[O:31])[CH2:28][C@H:29]3[O:35][C@@H:30]23)[CH:14]=[C:13]([F:12])[C:18]=1[F:19]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 69075122HCID 69075122, compound

Product 2

HCID 86612714HCID 86612714, compoundHCID 86612715HCID 86612715, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (1.04 g) was added to a solution of (6S*,9aR*)-6-(3,4,5-trifluorophenyl)-1,2,3,6,9,9a-hexahydroquinolizin-4-one (681 mg) in methylene chloride (30 mL), and the reaction solution was stirred at room temperature for three days. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain (1aR*,2R*,6aR*,7aS*)-2-(3,4,5-trifluorophenyl)octahydro-1-oxa-2a-aza-cyclopropa[b]naphthalen-3-one (283 mg) and (1aS*,2R*,6aR*,7aR*)-2-(3,4,5-trifluorophenyl)octahydro-1-oxa-2a-aza-cyclopropa[b]naphthalen-3-one (235 mg). The physical properties of (1aR*,2R*,6aR*,7aS*)-2-(3,4,5-trifluorophenyl)octahydro-1-oxa-2a-aza-cyclopropa[b]naphthalen-3-one are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-a27059f5c82a4af68e6979aea9a45165
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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