(R)-Pyrrolidin-3-ylmethanol Chemical Properties

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)

form 

powder

color 

Yellow

Water Solubility 

Slightly soluble in water.

Sensitive 

Hygroscopic

InChI

InChI=1S/C5H11NO/c7-4-5-1-2-6-3-5/h5-7H,1-4H2/t5-/m1/s1

InChIKey

QOTUIIJRVXKSJU-RXMQYKEDSA-N

SMILES

N1CC[C@@H](CO)C1

Safety Information

Hazard Codes 

F,C

Risk Statements 

36/37/38

Safety Statements 

26-37-60

TSCA 

No

HS Code 

2933998090

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

Uses

It is an intermediate in organic syntheses.

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. After the dropwise addition was completed, the reaction mixture was stirred at room temperature for 10 minutes and then heated to reflux the reaction for about 4 hours. Upon completion of the reaction, the reaction was quenched by addition of water, extracted with ethyl acetate and concentrated to give a light yellow oily liquid. The oily liquid was dissolved in ethanol, cooled to 20°C and then 500 g of sodium borohydride was added and the reaction was refluxed for 2 hours. The reaction was again quenched with water, 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

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