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

HRID 2066539Notes

Reaction equation

HRID 2066539 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=C(C=CC=1)C(OO)=[O:19]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]2[CH:12]([O:19]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-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (6.27 g, 34.2 mmol) in dichloromethane (35 mL) cooled down to 0° C. was added dropwise a solution of m-chloroperoxybenzoic acid (8.65 g, 1.1 eq) in dichloromethane (50 mL). The mixture stirred at room temperature for 4 hours. The mixture was partitioned between dichloromethane and 5% potassium carbonate solution. The combined organic layers were washed with brine, separated and dried (MgSO4). The crude product was purified by column chromatography to yield a (±)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester (4.43 g) as a pale yellow liquid.

Workup

  1. customThe mixture was partitioned between dichloromethane and 5% potassium carbonate solution
  2. washThe combined organic layers were washed with brine
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-8874d59780994b3d8e4d4502753cf96f
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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