ChemicalBook CAS DataBase List 3-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

3-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER synthesis

8synthesis methods

Product Name:3-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
CAS Number:177947-96-5
Molecular formula:C9H15NO3
Molecular Weight:185.22

142253-56-3

3-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

177947-96-5

The general procedure for the synthesis of tert-butyl 3-formylazetidine-1-carboxylate from 1-Boc-3-hydroxymethylazetidine was as follows: to a stirred solution of oxalyl chloride (4.28 mL, 49.8 mmol) in dichloromethane (DCM, 5 mL) was added slowly and dropwise to dimethylsulfoxide (DMSO, 0.71 mL, 9.96 mmol) at -78 °C. The reaction mixture was continued to be stirred at this temperature for 15 minutes. Subsequently, tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (0.69 g, 3.69 mmol) was added and triethylamine (2.1 mL, 14.75 mmol) was added immediately. The reaction system was gradually warmed to room temperature and diluted with DCM (30 mL). The reaction solution was washed with water and the organic phase was dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (using an Isolute column, eluent: heptane/ethyl acetate gradient, 0-100%) to give tert-butyl 3-formylazetidine-1-carboxylate (0.19 g, 27% yield).

142253-56-3 Synthesis

142253-56-3
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$6.00/1g

177947-96-5
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$11.00/100mg

Yield:177947-96-5 99%

Reaction Conditions:

with 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in ethyl acetateReflux;

Steps:

1 tert-butyl 3-formylazetidine-1-carboxylate (1.3)
To a stirringsolutionof tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate(20.96 g, 112 mmol) in EA (500 ml)was added IBX (62.69 g, 224 mmol) and the reaction was refluxed overnight. The reaction was cooledto rt, PE (500 ml)was added and the reaction mixture was filtered. The filtrate was concentrated under reduced pressureto give compound1.3 as yellow oil product (20.56 g,99%). 1H NMR (400 MHz, CDCI3) i5 1.44 (s, 9 H), 3.32-3.4015 (m, 1 H), 4.07-4.14 (m, 4 H), 9.85 (d, J = 2.0Hz, 3 H).

References:

ACHAOGEN, INC.;LINSELL, Martin Sheringham;AGGEN, James Bradley;DOZZO, Paola;HILDEBRANDT, Darin James;COHEN, Frederick;KASAR, Ramesh Annasaheb;KANE, Timothy Robert;GLIEDT, Micah James;MCENROE, Glenn A. WO2014/165075, 2014, A1 Location in patent:Page/Page column 45; 46

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610791-05-4 Synthesis