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

Boiling point:

257℃

Density 

1.188

refractive index 

1.4600 to 1.4640

Flash point:

109℃

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

clear liquid

pka

-2.70±0.40(Predicted)

color 

Colorless to Light yellow

Sensitive 

Air Sensitive

InChI

InChI=1S/C9H15NO3/c1-9(2,3)13-8(12)10-4-7(5-10)6-11/h6-7H,4-5H2,1-3H3

InChIKey

JVQOZRRUGOADSU-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CC(C=O)C1

Safety Information

Hazard Codes 

Xi

HS Code 

2933998090

3-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Chemical Properties

3-Formylazetidine-1-carboxylic acid tert-butyl ester is a white to pale yellow solid compound with high reactivity and selectivity, which can be used to prepare a variety of compounds with specific functions.

Uses

1-Boc-azetidine-3-carboxaldehyde is used as a starting material in organic synthesis. It is also used as an intermediate in pharmaceuticals.

Synthesis

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).

References

[1] Patent: WO2014/165075, 2014, A1. Location in patent: Page/Page column 45; 46
[2] Patent: US2014/171402, 2014, A1. Location in patent: Paragraph 0053; 0054; 0055; 0056
[3] Patent: EP2754653, 2014, A2. Location in patent: Paragraph 0044; 0045
[4] Patent: WO2018/89355, 2018, A1. Location in patent: Page/Page column 102-104
[5] Patent: WO2010/80357, 2010, A1. Location in patent: Page/Page column 45-46

3-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(177947-96-5)Related Product Information

• Methyl 3-formylbenzoate
• 2-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• (R)-2-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 3-(2-CYANO-ACETYL)-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 3-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 1-N-Boc-3-Azetidinecarboxylic acid
• AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-ETHYL ESTER
• Methyl 1-Boc-azetidine-3-carboxylate