2-HYDROXYMETHYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

270.3±13.0 °C(Predicted)

Density 

1.115±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.77±0.10(Predicted)

Safety Information

HS Code 

2933998090

2-HYDROXYMETHYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Uses

[1-(tert-Butoxycarbonyl)azetidin-2-yl]methanol is used as a potential positiron emission tomography imaging agents for nicotinic acetylcholine receptors.

Synthesis

General procedure for the synthesis of tert-butyl 2-hydroxymethyl-azetidine-1-carboxylate from N-Boc-azetidine-2-carboxylic acid: to a solution of N-Boc-azetidine-2-carboxylic acid (1.45 g, 7.21 mmol) in anhydrous THF (12 mL) was added slowly and dropwise borane-methyl sulfide complex (10 M, 3 mL) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred for 3 hours. Upon completion of the reaction, the reaction was quenched with methanol (10 mL) followed by dilution of the reaction mixture with dichloromethane (100 mL). The organic phase was washed with water (40 mL x 3), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford tert-butyl 2-hydroxymethyl-azetidine-1-carboxylate (1.25 g) as a colorless oil.MS-ESI (m/z): 132.0 [M+1-56]+.

References

[1] Patent: WO2015/7219, 2015, A1. Location in patent: Page/Page column 38

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