Triethylamine → 5-Acetyl-7a-pyrrolidin-1-yl-3a,4,5,6,7,7a-hexahydro-isoxazolo[4,5-c]pyridine-3-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:9])[C:5](=[N:7][OH:8])Cl)[CH3:2].[N:10]1([C:15]2[CH2:16][CH2:17][N:18]([C:21](=[O:23])[CH3:22])[CH2:19][CH:20]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:5]1[CH:20]2[CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17][CH2:16][C:15]2([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[O:8][N:7]=1)=[O:9])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 17.9 g (0.118 mol) of 2-chlorohydroxyiminoacetic acid ethyl ester in 20 mL of DCM was added to a solution of 16.3 g (84 mmol) of 1-(4-pyrrolidin-1-yl-3,6-dihydro-2H-pyridin-1-yl)-ethanone (A) in 150 mL of DCM. On so doing, the solution warmed up and turned red. After cooling to 0° C. (ice bath), 16.4 g (0.118 mol) of triethylamine were slowly added dropwise with stirring. The mixture was stirred for 12 h at RT and then washed, firstly with 10% (weight percent) citric acid solution in water, and then with sat. aq. common salt solution. After removal of the solvent under a vacuum, the residue was purified by column chromatography (SiO2, EtOAc/EtOH 9:1). 18.5 g (71% of theoretical) of the desired product 5-acetyl-7a-pyrrolidin-1-yl-3a,4,5,6,7,7a-hexahydro-isoxazolo[4,5-c]pyridine-3-carboxylic acid ethyl ester (B) were obtained in the form of a brown oil.
Workup
- temperaturethe solution warmed up
- additionwere slowly added dropwise
- stirringThe mixture was stirred for 12 h at RT
- washwashed, firstly with 10% (weight percent) citric acid solution in water
- customAfter removal of the solvent under a vacuum
- customthe residue was purified by column chromatography (SiO2, EtOAc/EtOH 9:1)
Sources & evidence
- ORD record
- ord-1e5a6f52b7534dbabce4a3f1c8d363cd
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08048879B2
Reaction notes
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