m-Chloroperbenzoic acid → Naphthalen-2-ylmethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

HRID 1095713Notes

Reaction equation

HRID 1095713 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:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)=[O:19])[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]1>C(Cl)Cl>[CH:14]12[O:9][CH:15]1[CH2:16][CH2:17][N:12]([C:18]([O:20][CH2:21][C:22]1[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=1)=[O:19])[CH2:13]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66781418naphthalen-2-ylmethyl 5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 86638609Naphthalen-2-ylmethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of mCPBA (13.02 g, 58.13 mmol) dissolved in methylene chloride (50 mL) was added dropwise to a cooled (0° C.) solution of naphthalen-2-ylmethyl 5,6-dihydropyridine-1(2H)-carboxylate (11 g, 41.5 mmol) dissolved in methylene chloride (33 mL). The solution was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched with 5% K2CO3 and then the layers were separated. The organic phase was washed with 5% K2CO3, saturated NaCl, dried over Na2SO4and concentrated in vacuo (9.5 g).

Workup

  1. additionwas added dropwise to
  2. customThe reaction was quenched with 5% K2CO3
  3. customthe layers were separated
  4. washThe organic phase was washed with 5% K2CO3, saturated NaCl
  5. customdried over Na2SO4and
  6. concentrationconcentrated in vacuo (9.5 g)

Sources & evidence

ORD record
ord-830d73aa760d4f2398609e19587ab489
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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