Prolinol

Prolinol
Names
	IUPAC name (R/S) 2-pyrrolidinemethanol
Identifiers
CAS Number	68832-13-3 (D-prolinol) ; 23356-96-9 (L-prolinol) ;
3D model (JSmol)	(D-prolinol): Interactive image; (L-prolinol): Interactive image;
ChemSpider	2006673 (D-prolinol) ; 555468 (L-prolinol) ;
ECHA InfoCard	100.157.355
PubChem CID	2724541 (D-prolinol); 640091 (L-prolinol);
CompTox Dashboard (EPA)	DTXSID301020303 DTXSID00988536, DTXSID301020303 ;
	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
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Irritant
Flash point	86 °C (187 °F; 359 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.^[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]

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).
^ Enders D.; Fey P.; Kipphardt, H. [1] Organic Syntheses, Collected Volume 8, p.26 (1993).
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[1]

[2]

[3]

[4]

Preparation

Use

See also

References