| Identification | More | [Name]
(R)-3-Hydroxypyrrolidine | [CAS]
2799-21-5 | [Synonyms]
3-PYRROLIDINOL, (R)
(3R)-3-PYRROLIDINOL
(R)-(+)-3-HYDROXYPYRROLIDINE
(R)-3-HYDROXYPYRROLIDINE
(R)-(+)-3-PYRROLIDINOL
(R)-3-PYRROLIDINOL
R-(-)-3-PYRROLIDINOL
R-HP
(R)-PYRROLIDIN-3-OL
(3R)-Pyrrolidin-3-ol
R-(+)-3-PYRROLIDINOL 98%
(R)-(+)-3-HYDROXYPYRROLIDINE , EE 99%
(R)-(+)-3-Hydroxypyrrolidine, 99%, ee 99%
(3R)-Pyrrolidine-3-ol
(R)-Pyrrolidine-3-ol | [EINECS(EC#)]
628-839-3 | [Molecular Formula]
C4H9NO | [MDL Number]
MFCD00145220 | [Molecular Weight]
87.12 | [MOL File]
2799-21-5.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow to orange-brown viscous liquid | [Melting point ]
15°C | [alpha ]
6.5 º (c=3.5% in MeOH) | [Boiling point ]
215-216 °C (lit.) | [density ]
1.078 g/mL at 20 °C(lit.)
| [refractive index ]
n20/D 1.488(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [form ]
Viscous Liquid | [pka]
14.91±0.20(Predicted) | [color ]
Clear yellow to orange-brown | [Specific Gravity]
1.048 | [Optical Rotation]
[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) | [Storage Precautions]
Air sensitive |
| Hazard Information | Back Directory | [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 |
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