Hydrochloric Acid → Tert-butyl 3-formylazetidine-1-carboxylate
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:21][CH:20]([CH2:22][OH:23])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C.Cl>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[CH2:21][CH:20]([CH:22]=[O:23])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Oxalyl chloride (2.1 mL; 24.0 mmol) was dissolved in methylene chloride (30 mL) and cooled to -78° C. Dimethyl sulfoxide (2.3 mL; 32.0 mmol) was added. A solution of 3-hydroxymethylazetidine-1-carboxylic acid tert-butyl ester (3.0 g; 16.0 mmol) in methylene chloride (20 mL) was added dropwise to the reaction mixture. Triethyl amine (11.1 mL; 80.1 mmol) was added and the reaction mixture was heated to room temperature. Methylene chloride (200 mL) and hydrochloric acid (200 mL; 1 N) was added. The aqueous phase was extracted with methylene chloride (100 mL). The combined organic phases were washed with saturated sodium hydrogen carbonate (100 mL), dried (magnesium sulfate) and evaporated in vacuo. The residue was chromatographed on silica (3×30 cm) using ethyl acetate/heptane (4:1) as eluent to afford 1.11 g of 3-formylazetidine-1-carboxylic acid tert-butylester.
Workup
- temperaturethe reaction mixture was heated to room temperature
- extractionThe aqueous phase was extracted with methylene chloride (100 mL)
- washThe combined organic phases were washed with saturated sodium hydrogen carbonate (100 mL)
- dry with materialdried (magnesium sulfate)
- customevaporated in vacuo
- customThe residue was chromatographed on silica (3×30 cm)
Sources & evidence
- ORD record
- ord-23109aba24104b0b885e5d108ea17529
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06127391
Reaction notes
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