(S)-Pyrrolidin-3-ylmethanol Chemical Properties

Melting point:

174-176℃

Boiling point:

176 °C

Density 

0.978

Flash point:

90 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

14.93±0.10(Predicted)

Appearance

Colorless to off-white Solid-liquid mixture

optical activity

Consistent with structure

Water Solubility 

Slightly soluble in water

Sensitive 

Hygroscopic

CAS DataBase Reference

110013-19-9

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37-60

TSCA 

No

HS Code 

2933998090

(S)-Pyrrolidin-3-ylmethanol Usage And Synthesis

Uses

(S)-Pyrrolidin-3-ylmethanol is used in the preparation of pyridoindoles as kinase inhibiting compounds useful in treatment and prevention of kinase-associated diseases.

Synthesis

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

References

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

(S)-Pyrrolidin-3-ylmethanol(110013-19-9)Related Product Information

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• 4-(4-METHOXYPHENYL)PYRROLIDINE-3-METHYLCARBOXYLATE
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