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(R)-3-Hydroxypyrrolidine

Product Name(R)-3-Hydroxypyrrolidine
CAS2799-21-5
MFC4H9NO
MW87.12
EINECS628-839-3
MOL File2799-21-5.mol

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
InChI	1S/C4H9NO/c6-4-1-2-5-3-4/h4-6H,1-3H2/t4-/m1/s1
InChIKey	JHHZLHWJQPUNKB-SCSAIBSYSA-N
SMILES	O[C@@H]1CCNC1
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
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

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

51-35-4

40499-83-0

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

Chemical Properties

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MSDS

Usage And Synthesis

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