m-Chloroperbenzoic acid → tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

HRID 1602187Notes

Reaction equation

HRID 1602187 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:22])C=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]2[O:22][CH:12]2[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 21991116tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-tert-butoxycarbonyl-1,2,3,6-tetrahydropyrdine (23.6 g, 129 mmol), and m-chloroperbenzoic acid (46 g, 193 mmol) in dichloromethane (600 ml) at 0° C. was stirred and allowed to reach room temperature overnight. Washing with 5% aqueous sodium sulfite (700 ml), 3% aqueous sodium hydrogen carbonate (700 ml), 1 M aqueous sodium hydroxide (700 ml), and, finally, water (700 ml). Drying and evaporation was followed by purification by column chromatography on silica gel with 3% ethanol in dichloromethane. The title compound was obtained as a colorless oil. Yield 8.4 g, 33%.

Workup

  1. washWashing with 5% aqueous sodium sulfite (700 ml), 3% aqueous sodium hydrogen carbonate (700 ml), 1 M aqueous sodium hydroxide (700 ml)
  2. customDrying
  3. customevaporation
  4. customwas followed by purification by column chromatography on silica gel with 3% ethanol in dichloromethane

Sources & evidence

ORD record
ord-1120bb301c47428080ff867513c9b1f2
Source dataset
uspto-grants-1999_11
Patent number
US05981539

Reaction notes

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