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

HRID 451801Notes

Reaction equation

HRID 451801 reaction equation
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:22]>C(Cl)Cl.CCOCC>[CH:3]12[O:22][CH:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])[CH2:2]2

Participants

5

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-carboxylateYield 74%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl 5,6-dihydropyridine-1(2H)-carboxylate (9.93 g, 45.76 mmol) in CH2Cl2 (75 mL) was cooled to 0° C. Solid m-chloroperoxybenzoic acid (77%, 15.38 g, 1.5 equiv) was added. After 10 min, the reaction mixture was warmed slowly to rt. A white precipitate formed after 1 h. The reaction was complete after an additional hour of stirring. The mixture was diluted with ether (300 mL), washed by with 5% aq NaOH (2×40 mL), 25% aq Na2S2O3 solution (3×20 mL) and brine (30 mL), and dried over Na2SO4. After concentration, the residue was purified by flash chromatography to afford benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (7.87 g, 74% yield). MS ESI +ve m/z 234 (M+1).

Workup

  1. customA white precipitate formed after 1 h
  2. waitThe reaction was complete after an additional hour
  3. washwashed by with 5% aq NaOH (2×40 mL), 25% aq Na2S2O3 solution (3×20 mL) and brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0bfde5d720d94af58a3d2bdf8262237c
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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