ChemicalBook CAS DataBase List 1-(Tert-butoxycarbonyl)-3-(methanesulfonyloxy)azetidine

1-(Tert-butoxycarbonyl)-3-(methanesulfonyloxy)azetidine synthesis

5synthesis methods

Product Name:1-(Tert-butoxycarbonyl)-3-(methanesulfonyloxy)azetidine
CAS Number:141699-58-3
Molecular formula:C9H17NO5S
Molecular Weight:251.3

124-63-0
6 suppliers
$10.00/5g

141699-55-0 Synthesis

141699-55-0
384 suppliers
$6.00/1g

1-(Tert-butoxycarbonyl)-3-(methanesulfonyloxy)azetidine

141699-58-3
110 suppliers
$6.00/250mg

Yield:141699-58-3 100%

Reaction Conditions:

with triethylamine in tetrahydrofuran at 20; for 2 h;Inert atmosphere;

Steps:

26.2 tert-Butyl 3-((methylsulfonyl)oxy)azetidine-1-carboxylate
Production Example 26-2
tert-Butyl 3-((methylsulfonyl)oxy)azetidine-1-carboxylate
Methanesulfonyl chloride (2.57 mL, 33.3 mmol) and triethylamine (11.6 mL, 83.1 mmol) were added to a solution of commercially available N-BOC-3-hydroxy azetidine (4.8 g, 27.7 mmol) in tetrahydrofuran (100 mL) under nitrogen atmosphere at room temperature.
The reaction liquid was stirred at room temperature for 2 hours.
A saturated aqueous sodium bicarbonate solution was added to the reaction liquid at room temperature, and the mixture was diluted with ethyl acetate.
The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate.
The drying agent was separated by filtration and then the filtrate was concentrated under vacuum.
The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-1:1) to quantitatively obtain the title compound.
¹H-NMR Spectrum (CDCl₃) δ (ppm): 1.45 (9H, s), 3.07 (3H, s), 4.03-4.18 (2H, m), 4.22-4.36 (2H, m), 5.12-5.27 (1H, m).

References:

Eisai R&D Management Co., Ltd.;Funasaka, Setsuo;Okada, Toshimi;Tanaka, Keigo;Nagao, Satoshi;Ohashi, Isao;Yamane, Yoshinobu;Nakatani, Yusuke;Karoji, Yuki US2014/235614, 2014, A1 Location in patent:Paragraph 0570; 0571; 0572

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24424-99-5 Synthesis