m-Chloroperbenzoic acid → Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

HRID 1499466Notes

Reaction equation

HRID 1499466 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[N:12]1([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:17][CH:16]=[CH:15][CH2:14][CH2:13]1>C(Cl)Cl>[CH:16]12[O:9][CH:15]1[CH2:14][CH2:13][N:12]([C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])[CH2:17]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11458613Benzyl 5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 13186888Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (14.6 g, 63.3 mmol) was added slowly to a stirred solution of benzyl 3,6-dihydropyridine-1(2H)-carboxylate (12.50 g, 57.5 mmol) in DCM (80 mL) which was cooled in an ice bath. The reaction mixture was allowed to warm to room temperature and stirred for 16 h. The reaction mixture was then quenched with aq. Na2CO3 and the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the sub-title compound. LCMS calc. for C13H16NO3 (M+H)+: m/z=234.1. Found: 234.0.

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe reaction mixture was then quenched with aq. Na2CO3
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-daeb57a57e564901a17516b7756ea4f6
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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