(S)-3-Hydroxypyrrolidine hydrochloride Chemical Properties

Melting point:

104-107°C

Boiling point:

108-110℃/8mm

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Sparingly), Methanol (Slightly)

form 

Solid

color 

Off-White to Pale Beige

Stability:

Hygroscopic

InChI

InChI=1/C4H9NO.ClH/c6-4-1-2-5-3-4;/h4-6H,1-3H2;1H/t4-;/s3

InChIKey

QPMSJEFZULFYTB-NDILARRWNA-N

SMILES

O[C@@H]1CNCC1.Cl |&1:1,r|

CAS DataBase Reference

122536-94-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

-36/37/38

Safety Statements 

26-37

HS Code 

29339900

(S)-3-Hydroxypyrrolidine hydrochloride Usage And Synthesis

Chemical Properties

almost white crystalline powder

Uses

(S)-3-Hydroxypyrrolidine Hydrochloride is a useful intermediate for the synthesis of Asimadoline Hydrochlorine (A788250), used in the treatment of IBS, a disorder associated with pain and altered bowel function.

Synthesis

(3S)-N-benzyl-3-hydroxypyrrolidine-2,5-dione (100g), added to a 1L high-pressure reactor, add ethanol 500mL, add 10% palladium carbon (58% water content, model D10H5A, Shaanxi Ruike New Materials Co., Ltd.) 5g, through the hydrogen, keep the pressure of the reaction system 0.5MPa, slowly raise the temperature to 70 ??, the reaction for 5 hours. The reaction was completed by central control, filtered to recover the palladium carbon, concentrated the solvent, added isopropanol (200 mL) to the residue and stirred to dissolve completely, added concentrated hydrochloric acid (45 mL, 12M, 1.1eq) dropwise, stirred overnight at room temperature, and filtered to obtain a white solid, i.e., 51g of (S)-3-pyrrolidinol hydrochloride, with 85% yield and 99.1% purity.

References

[1] Patent: EP2803664, 2014, A1. Location in patent: Paragraph 0153; 0154
[2] Patent: US2015/5282, 2015, A1. Location in patent: Paragraph 0224; 0225
[3] Patent: CN105646321, 2016, A. Location in patent: Paragraph 0031; 0032

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