ChemicalBook CAS DataBase List tert-butyl 3-(pyridin-2-yl)azetidine-1-carboxylate

tert-butyl 3-(pyridin-2-yl)azetidine-1-carboxylate synthesis

6synthesis methods

Product Name:tert-butyl 3-(pyridin-2-yl)azetidine-1-carboxylate
CAS Number:206446-39-1
Molecular formula:C13H18N2O2
Molecular Weight:234.29

109-04-6 Synthesis

109-04-6
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1-t-Butoxycarbonylazetedin-3-ylzinc iodide, 0.50 M in THF

206446-38-0
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tert-butyl 3-(pyridin-2-yl)azetidine-1-carboxylate

206446-39-1
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Yield:206446-39-1 80%

Reaction Conditions:

Stage #1: (1-(tert-butoxycarbonyl)azetidin-3-yl)zinc(II) iodidewith tetrakis(triphenylphosphine) palladium⁽⁰⁾ in tetrahydrofuran at 20; for 0.166667 h;Inert atmosphere;
Stage #2: 2-bromo-pyridine in tetrahydrofuran at 65; for 2 h;Inert atmosphere;

Steps:

2

In a three-necked reaction flask equipped with a stirrer, 42.5 g of zinc powder and 10.8 g of 1,2-dibromoethane were added, 100 ml Tetrahydrofuran, and then heated to 65 ° C drop of trace trimethylchlorosilane 6 grams and stirring for half an hour, cooling to room temperature. 3-iodo-N-t-butoxycarbonyl-azetidine 142 g of tetrahydrofuran 250 ml was added dropwise to the above solution at a temperature not exceeding 30 ° C, Tetrakylphenylphosphine palladium in tetrahydrofuran 60 ml was added dropwise to the above solution under nitrogen atmosphere and stirred at room temperature for 10 minutes, followed by dropwise addition of 95 g of 2-bromopyridine in 100 ml of tetrahydrofuran under nitrogen atmosphere. The reaction system The temperature was raised to 65 ° C and held for 2 hours. Cooling, suctioning, ethyl acetate 1000 ml dilution, saturated sodium bicarbonate 500 ml washing twice, 500 ml of saline washed twice, anhydrous sodium sulfate 100 grams dry, filtered, the filtrate was concentrated in vacuo, the oil through the fast column To give 94 g of 2- (3-tert-butoxycarbonylazetidinyl) pyridine as a brown oil in 80% yield and 98% purity.

References:

CN106957300,2017,A Location in patent:Paragraph 0039; 0040

109-04-6 Synthesis

109-04-6
525 suppliers
$6.00/25g