Prolinol

Prolinol

Names
IUPAC name (R or S) 2-pyrrolidinemethanol
Identifiers
CAS Number	68832-13-3 (D-prolinol) Y 23356-96-9 (L-prolinol) N
ChemSpider	2006673 (D-prolinol) N 555468 (L-prolinol) N
Jmol 3D model	(D-prolinol): Interactive image (L-prolinol): Interactive image
PubChem	2724541 (D-prolinol) 640091 (L-prolinol)
InChI (D-prolinol): InChI=1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m1/s1 Key: HVVNJUAVDAZWCB-RXMQYKEDSA-N (L-prolinol): InChI=1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m0/s1 Key: HVVNJUAVDAZWCB-YFKPBYRVSA-N
SMILES (D-prolinol): C1C[C@@H](NC1)CO (L-prolinol): C1C[C@H](NC1)CO
Properties
Chemical formula	C5H11NO
Molar mass	101.15 g/mol
Appearance	Liquid
Density	1.036 g/mL liquid
Boiling point	74 to 76 °C (165 to 169 °F; 347 to 349 K) at 2 mmHg
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

This article is about a compound used in synthesis of certain stimulants and should not be confused with a stimulant in that class the brand name of which is propalin

Prolinol is a chiral amino-alcohol that is used as a chiral building block in organic synthesis. It exists as two enantiomers: the D and L forms.

Preparation

Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydride. Because proline is cheaply available in high optical purity, enantiomerically pure prolinol is also widely available.

Use

Prolinol is used in broad variety of chemical reactions as chiral ligand, chiral catalyst or chiral auxiliary reagent in the Hajos-Parrish-Eder-Sauer-Wiechert reaction, the Baylis-Hillman reaction, Noyori type reaction and the Michael reaction.

See also

• Chiral synthesis