Tert-butyl 3-hydroxyazetidine-1-carboxylate → 3-Oxo-azetidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CS(C)=O>[O:12]=[C:10]1[CH2:11][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
A 5 L-3-neck flask equipped with mechanical stirrer, thermocouple, addition funnel and nitrogen inlet was charged with Py-SO3 (277 g, 1.74 mol) and DMSO (900 mL) and cooled to 10° C. in ice-bath. TEA (177 g/244 mL, 1.74 mol) was added. A solution of tert-butyl-3 hydroxyazetidine-1-carboxylate (Preparation 1, 100.8 g, 0.58 mol) in DMSO (500 mL) was added slowly via addition funnel at 10° C. The reaction was stirred at ambient temperature overnight. GC/MS analysis of the reaction mixture reveals that the reaction was completed. The reaction was quenched with brine (1 L). Solids were filtered and the aqueous was extracted with ethyl acetate (3×1 L). The combined organics were washed with saturated aqueous NaHCO3 (1.5 L), brine (1.5 L), dried over sodium sulfate, filtered, and concentrated to give the desired product (94 g, 95% yield). 1H NMR (CDCl3) δ 4.6 (s, 4H), 1.4 (s, 9H).
Workup
- customA 5 L-3-neck flask equipped with mechanical stirrer
- additionthermocouple, addition funnel and nitrogen inlet
- customThe reaction was quenched with brine (1 L)
- filtrationSolids were filtered
- extractionthe aqueous was extracted with ethyl acetate (3×1 L)
- washThe combined organics were washed with saturated aqueous NaHCO3 (1.5 L), brine (1.5 L)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d41420fb37674f70be7fb0cac9d3f59f
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415310B2
Reaction notes
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