Triethylamine → 8-Tert-butyl-1-oxa-2-azaspiro[4.5]dec-2-ene-3-carboxylic acid ethyl ester

HRID 1013328Notes

Reaction equation

HRID 1013328 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[C:5](Cl)=[N:6][OH:7])[CH3:2].[C:10]([CH:14]1[CH2:19][CH2:18][C:17](=[CH2:20])[CH2:16][CH2:15]1)([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:1]([O:3][C:4]([C:5]1[CH2:20][C:17]2([CH2:18][CH2:19][CH:14]([C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:15][CH2:16]2)[O:7][N:6]=1)=[O:9])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 139425Cyclohexane, 1-(1,1-dimethylethyl)-4-methylene-HCID 6816376Ethyl chloro(hydroximino)acetate

Product 1

HCID 579514518-Tert-butyl-1-oxa-2-azaspiro[4.5]dec-2-ene-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2-chloro-2-hydroxyiminoacetic acid ethyl ester (2.2 g, 14.6 mmol) in DCM (20 ml) was slowly added dropwise at 0° C. to a solution of 1-tert-butyl-4-methylenecyclohexane (740 mg, 4.86 mmol) in DCM (20 ml). Subsequently, a solution of triethylamine (1.5 ml) in DCM (10 ml) was slowly added dropwise at 0° C. and the resulting mixture was stirred overnight at RT. The reaction mixture was diluted with water. The aqueous phase was extracted several times with DMC. The combined organic phases were dried and the solvent was removed under vacuum. After purification of the residue (silica gel, hexane/ether 2:1) by column chromatography, the desired product 8-tert-butyl-1-oxa-2-azaspiro[4.5]dec-2-ene-3-carboxylic acid ethyl ester was obtained as a yellowish liquid (1.21 g, 93% of the theoretical amount).

Workup

  1. extractionThe aqueous phase was extracted several times with DMC
  2. customThe combined organic phases were dried
  3. customthe solvent was removed under vacuum
  4. customAfter purification of the residue (silica gel, hexane/ether 2:1) by column chromatography

Sources & evidence

ORD record
ord-566452ae43d8471fbbe1319fa0c3a372
Source dataset
uspto-grants-2011_07
Patent number
US07981883B2

Reaction notes

Loading…