3-HYDROXY-3-PHENYLAZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER synthesis
- Product Name:3-HYDROXY-3-PHENYLAZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
- CAS Number:398489-25-3
- Molecular formula:C14H19NO3
- Molecular Weight:249.31
398489-26-4
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$9.00/5g
108-86-1
519 suppliers
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398489-25-3
35 suppliers
$170.00/250MG
Yield:398489-25-3 94%
Reaction Conditions:
Stage #1: bromobenzene in tetrahydrofuran at -78; for 0.166667 h;Inert atmosphere;
Stage #2: with n-butyllithium in tetrahydrofuran;hexane; for 1 h;Inert atmosphere;
Stage #3: tert-butyl 3-oxoazetidine-1-carboxylate in tetrahydrofuran at 20;Inert atmosphere;
Steps:
N-Boc-3-aryl-azetidin-3-ol (4). General Procedure.
General procedure: The corresponding halogenated bromobenzene (3 equiv) was dissolved in anhydrous THF (10mL) and cooled to -78 °C for 10 minutes. A solution of n-butyllithium (2.5M in hexane, 3 equiv) was added dropwise and the reaction mixture was stirred for 1 h under nitrogen. N-Boc-3-azetidinone (1 equiv) was dissolved in anhydrous THF (1 mL), and added via syringe to the reaction mixture. The mixture was stirred overnight and allowed to warm to room temperature.The reaction was quenched with cold 10% NH4Cl (10 mL, 0 °C), extracted with diethyl ether (3x 50 mL). The combined organic portions were washed with brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by column chromatography (SiO2, 30% ethyl acetate:hexanes) to afforded the desired N-Boc-3-arylazetidin-3-ol (4).
References:
Thaxton, Amber;Izenwasser, Sari;Wade, Dean;Stevens, Edwin D.;Mobley, David L.;Jaber, Vivian;Lomenzo, Stacey A.;Trudell, Mark L. [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 15,p. 4404 - 4407] Location in patent:supporting information
398489-26-4
442 suppliers
$9.00/5g
100-58-3
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$18.00/10ml
398489-25-3
35 suppliers
$170.00/250MG
398489-26-4
442 suppliers
$9.00/5g
100-59-4
267 suppliers
$42.00/0.25mole
398489-25-3
35 suppliers
$170.00/250MG