m-Chloroperbenzoic acid → Tert-butyl 1-oxa-6-azaspiro[2.6]nonane-6-carboxylate

HRID 2387586Notes

Reaction equation

HRID 2387586 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C:11](=[CH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-:17].[Na+].ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C:11]2([O:17][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 46941824tert-Butyl 4-methylideneazepane-1-carboxylate

Product 1

HCID 57366410Tert-butyl 1-oxa-6-azaspiro[2.6]nonane-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to example 82 step 1 with 4-methylene-azepane-1-carboxylic acid tert-butyl ester (MW: 211.307, 1.73 mmol), 1.16 g sodium bicarbonate (MW: 84.01 13.8=01) and 1.36 g of 80% m-chloroperbenzoic acid (MW172.57, 6.05 mmol) in 5 ml of dichloromethane. Yield: 250 mg, 63%. MS: 228.8 (M+H)+, 127.8 (M-(CH3)3COCO) method ESI+.

Sources & evidence

ORD record
ord-400dcd084ef64a32a7b319892b49957e
Source dataset
uspto-grants-2012_09
Patent number
US08268812B2

Reaction notes

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