ChemicalBook CAS DataBase List N-CBZ-3-OXOAZETIDINE

N-CBZ-3-OXOAZETIDINE synthesis

5synthesis methods

Product Name:N-CBZ-3-OXOAZETIDINE
CAS Number:105258-93-3
Molecular formula:C11H11NO3
Molecular Weight:205.21

128117-22-6
139 suppliers
$10.00/1g

105258-93-3
138 suppliers
$6.00/1g

Yield:105258-93-3 99%

Reaction Conditions:

with Dess-Martin periodane in dichloromethane at 20; for 5 h;

Steps:

3
To a solution of phenylmethyl 3-hydroxyazetidine-l-carboxylate (3.5 g, 0.0168 mol) in dichloromethane (100 mL) was added Dess-Martin periodinane (10.7 g, 0.0.25 mol) at room temperature and stirred for 5 h. The reaction mixture was quenched with 1 :1 ratio of saturated aqueous sodium bicarbonate and IM sodium thiosulfate (200 mL) and then partitioned with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo to afford phenylmethyl 3-oxoazetidine-l-carboxylate (3.43 g, 99% yield) as a clear and colorless oil without further purification. ¹H NMR (400 MHz, CDCl₃): 7.39-7.31 (m, 5H), 5.17 (s, 2H), 4.77 (s, 4H). MS (EI) for Ci₁H₁₁NO₃: 205 (M⁺).

References:

EXELIXIS, INC. WO2007/44515, 2007, A1 Location in patent:Page/Page column 165

FullText

40320-60-3 Synthesis