Prolinol

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Prolinol

IUPAC name	(R or S) 2-pyrrolidinemethanol
Identifiers
CAS number	[68832-13-3] (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
Melting point	°C (? K)
Boiling point	74-76 °C at 2 mmHg
Solubility in water	? g/100 ml (?°C)
Viscosity	? cP at ?°C
Hazards
Main hazards	Irritant
R-phrases	36/37/38
S-phrases	26-36
Flash point	86 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.

1 Preparation
2 Use
3 See also
4 References

[edit] Preparation

Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydride.^[1] Because proline is cheaply available in high optical purity, enantiomerically pure prolinol is also widely available.

[edit] 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. ^[2]^[3]

[edit] See also

Chiral synthesis

[edit] References

^ 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).
^ Benjamin List (2002). "Proline-catalyzed asymmetric reactions". Tetrahedron 58 (28): 5573–5590. doi:10.1016/S0040-4020(02)00516-1.
^ 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.