Prolinol

Prolinol
IUPAC name (R or S) 2-pyrrolidinemethanol
Identifiers
CAS number	68832-13-3 Y,  (D-prolinol) [23356-96-9] (L-prolinol)
Properties
Molecular formula	C5H11NO
Molar mass	101.15 g/mol
Appearance	Liquid
Density	1.036 g/mL liquid
Boiling point	74-76 °C at 2 mmHg
Hazards
R-phrases	36/37/38
S-phrases	26-36
Main hazards	Irritant
Flash point	86 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.^[1][2] 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. ^[3][4]

See also

• Chiral synthesis

References

1. ^ Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. Reduction of α-Amino Acids: L-Valinol Organic Syntheses, Collected Volume 7, p.530 (1990).
2. ^ Enders D.; Fey P.; Kipphardt, H. [1] Organic Syntheses, Collected Volume 8, p.26 (1993).
3. ^ Benjamin List (2002). "Proline-catalyzed asymmetric reactions". Tetrahedron 58 (28): 5573–5590. doi:10.1016/S0040-4020(02)00516-1. 
4. ^ Shinichi Itsuno, Koichi Ito, Akira Hirao and Seiichi Nakahama (1984). "Asymmetric synthesis using chirally modified borohydrides. Part 2. Enantioselective reduction of ketones with polymeric (S)-prolinol–borane reagent". J. Chem. Soc., Perkin Trans. 1 (12): 2887–2895. doi:10.1039/P19840002887.