Diethyl Ether → Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

HRID 2203706Notes

Reaction equation

HRID 2203706 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]O)=O.[N:12]1([C:18]([O-:20])=O)[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]1.CC[O:23]CC>C(Cl)Cl>[CH:14]12[O:23][CH:15]1[CH2:16][CH2:17][N:12]([C:18]([O:7][CH2:5][C:4]1[CH:3]=[CH:2][CH:11]=[CH:10][CH:9]=1)=[O:20])[CH2:13]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 216913171,2,3,6-Tetrahydropyridine-1-carboxylate

Product 1

HCID 13186888Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chlorobenzoperoxoic acid (51.1 g, 228 mmol) was added portion wise to a solution of 5,6-dihydropyridine-1(2H)-carboxylate (33.0 g, 152 mmol) in DCM (200 mL) at 0° C. After 10 minutes at 0° C., the reaction was warmed to room temperature and stirred at room temperature for 4 hours. The reaction mixture was diluted with ether (800 mL), washed with 1N NaOH solution (2×200 mL), saturated N2SO3 solution (2×100 mL), brine (100 mL), dried (sodium sulfate) and concentrated in vacuo to give benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (35.0 g, 99%) as an oil.

Workup

  1. washwashed with 1N NaOH solution (2×200 mL), saturated N2SO3 solution (2×100 mL), brine (100 mL)
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ddb00c2aafcb4a20b5f8e3a19a54133f
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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