Chloroacetone → Azetidine-1,3-dicarboxylic acid 1-benzyl ester 3-(2-oxo-propyl)ester
Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C1OCCOCCOCCOCCOCCOC1.Cl[CH2:39][C:40](=[O:42])[CH3:41].C(=O)(O)[O-].[Na+]>C1COCC1>[O:42]=[C:40]([CH3:41])[CH2:39][O:16][C:15]([CH:13]1[CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:14]1)=[O:17]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To 321 mg (75% w/w, 1.37 mmol) azetidine-1,3-dicarboxylic acid monobenzyl ester in 10 mL dry THF were added 82 mg NaH (2.05 mmol, 60% dispersion in mineral oil), 182 mg 18-crown-6 (0.68 mmol), 328 μL chloroacetone (4.11 mmol), and the mixture was stirred at 60° C. for 6 hours. After cooling to room temperature, 10 mL 1 M sodium bicarbonate was added and the mixture was extracted with DCM (2×10 mL), the organic layers were combined and dried over Na2SO4. After filtration and evaporation of the solvent the product was purified by column chromatography (silica, heptane-EtOAc 1:1 to EtOAc).
Workup
- temperatureAfter cooling to room temperature
- extractionthe mixture was extracted with DCM (2×10 mL)
- dry with materialdried over Na2SO4
- filtrationAfter filtration and evaporation of the solvent the product
- customwas purified by column chromatography (silica, heptane-EtOAc 1:1 to EtOAc)
Sources & evidence
- ORD record
- ord-3055dc1c5e664f9aa6ee4592c978aaa0
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346816B2
Reaction notes
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