(R)-3-Hydroxypyrrolidine Chemical Properties

Melting point:

15°C

Boiling point:

215-216 °C (lit.)

alpha 

6.5 º (c=3.5% in MeOH)

Density 

1.078 g/mL at 20 °C (lit.)

refractive index 

n20/D 1.488(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Viscous Liquid

pka

14.91±0.20(Predicted)

Specific Gravity

1.048

color 

Clear yellow to orange-brown

optical activity

[α]20/D +6.5°, c = 3.5 in methanol

Water Solubility 

Soluble in water and methanol.

Sensitive 

Air Sensitive & Hygroscopic

BRN 

5376132

CAS DataBase Reference

2799-21-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

F 

10-34

Hazard Note 

Irritant

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(R)-3-Hydroxypyrrolidine Usage And Synthesis

Chemical Properties

clear yellow to orange-brown viscous liquid

Uses

(R)-Pyrrolidin-3-ol is used in preparation of allosteric BCR-ABL bifunctional proteolysis targeting chimera compounds.

Synthesis

The general procedure for the synthesis of 3-hydroxypyrrolidine from L-hydroxyproline is as follows: Example 1: Synthesis of (R)-3-pyrrolidinol To a 1 liter reaction vessel was added (4R)-hydroxy-L-proline (250 g, 1.907 mol), 2-cyclohexen-1-one (18.3 g, 0.1907 mol), and polyethylene glycol (750 mL, 400 average molar mass). The reaction was carried out by stirring the mixture under nitrogen protection at 150-160 °C. After 10 h, the reaction was judged complete when the reaction mixture changed from a suspension to a homogeneous phase. The yield of (R)-3-pyrrolidinol was 89.3% as determined by gas chromatographic analysis. Subsequently, the reaction solution was subjected to decompression distillation at the same temperature to collect fractions with boiling points of 100-120 °C (pressure 6-40 hPa) to give (R)-3-pyrrolidinol (120.4 g, 72.5% yield, 99.6% chemical purity, 99.9% optical purity ee).

Purification Methods

The (±)-isomer is purified by repeated distillation ( b 102-104o/12mm, 108-110o/18mm), and the (±)-picrate crystallises from EtOH with m 140-141o. The R(+)-enantiomer has b 70o/0.6mm and [] D +5.6o (c 3.63, MeOH). Its hydrochloride has a negative rotation and its dimethiodide has m 230o and [] 24 -8.02o. [Suyama & Kanno Yakugaku Zasshi (J Pharm Soc Japan) 85 531 1965, Uno et al. J Heterocycl Chem 24 1025 1987, Flanagan & Joullie Heterocycles 26 2247 1987, Beilstein 21 III/IV 44.]

References

[1] Chemistry Letters, 1986, p. 893 - 896
[2] Patent: CN105153133, 2018, B. Location in patent: Paragraph 0022; 0023; 0024; 0025; 0026
[3] Synthetic Communications, 1993, vol. 23, # 19, p. 2691 - 2699
[4] Synthetic Communications, 1994, vol. 24, # 10, p. 1381 - 1387
[5] Patent: US2005/222430, 2005, A1. Location in patent: Page/Page column 2

(R)-3-Hydroxypyrrolidine(2799-21-5)Related Product Information

• N-Vinyl-2-pyrrolidone
• N-Methyl-2-pyrrolidone
• Polyvinylpyrrolidone
• 3-Pyrrolidinol
• Povidone iodine
• Pyrrolidine
• SCOPOLAMINE N-OXIDE HYDROBROMIDE
• METHYL-2-PYRROLIDONE
• Boc-Hyp-OH
• (2S,4R)-1-Acetyl-4-hydroxypyrrolidine-2-carboxylic acid
• RETRORSINE
• BOC-HYP(BZL)-OH
• CYTOCHALASIN A
• N-Cbz-Hydroxy-L-proline
• SWAINSONINE
• cis-4-Hydroxy-D-proline
• DIHYDROCYTOCHALASIN B
• CYTOCHALASIN E