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

141699-55-0

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

141699-58-3

Preparation of Example 26-2: tert-butyl 3-((methylsulfonyl)oxy)azetidine-1-carboxylate Under a nitrogen atmosphere, methanesulfonyl chloride (2.57 mL, 33.3 mmol) and triethylamine (11.6 mL, 83.1 mmol) were sequentially added to a solution of tetrahydrofuran (100 mL) containing N-Boc-3-hydroxyazetidine (4.8 g, 27.7 mmol). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, saturated aqueous sodium bicarbonate solution was added to the reaction solution and the mixture was diluted with ethyl acetate. The organic layer was separated, washed with saturated brine and subsequently dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography (eluent ratio: n-heptane/ethyl acetate = 9:1 to 1:1) to quantitatively obtain N-Boc-3-methylsulfonyloxyazetidine. 1H-NMR (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).

124-63-0
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$10.00/5g

141699-55-0 Synthesis

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

141699-58-3
116 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

FullText

24424-99-5 Synthesis