3-Hydroxymethylpyrrolidine Chemical Properties

Boiling point:

165-171℃

Density 

0.979

Flash point:

86℃

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

14.93±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Water Solubility 

Slightly soluble in water

Sensitive 

Hygroscopic

BRN 

1420904

InChI

InChI=1S/C5H11NO/c7-4-5-1-2-6-3-5/h5-7H,1-4H2

InChIKey

QOTUIIJRVXKSJU-UHFFFAOYSA-N

SMILES

N1CCC(CO)C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

3-Hydroxymethylpyrrolidine Usage And Synthesis

Uses

3-?Pyrrolidinemethanoln is a useful reagent in preparation of orally active (heterocyclic aminomethyl)pyrazoloquinolines as potent PDE10 inhibitors for the management of schizophrenia.

Synthesis

The general procedure for the synthesis of 3-pyrrolidinemethanol from methyl 5-oxopyrrolidine-3-carboxylate is as follows: 2 kg of methyl 5-oxo-3-pyrrolidinecarboxylate is dissolved in 20 liters of tetrahydrofuran, and 1.9 kg of sodium borohydride is added in batches at room temperature. Subsequently, 3.9 kg of boron trifluoride ether solution was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was stirred at room temperature for 10 minutes and then heated to reflux for about 4 hours. Upon completion of the reaction, the reaction was quenched with water and extracted with ethyl acetate. The organic phases were combined and concentrated to give a light yellow oily liquid. This oily liquid was dissolved in ethanol, 500 g of sodium borohydride was added and heated to reflux for 2 hours. At the end of the reaction, the reaction was again quenched with water and extracted with ethyl acetate. The organic phase was washed sequentially with saturated aqueous sodium bicarbonate and saturated brine, and finally the organic phase was concentrated to give 1.2 kg of 3-pyrrolidinemethanol in 86% yield.

References

[1] Patent: CN106588738, 2017, A. Location in patent: Paragraph 0032; 0034; 0039; 0042; 0044

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