Prolinol

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.

Prolinol

Names
IUPAC name (R/S) 2-pyrrolidinemethanol
Identifiers
CAS Number	68832-13-3 (D-prolinol) Y 23356-96-9 (L-prolinol) N
3D model (JSmol)	(D-prolinol): Interactive image (L-prolinol): Interactive image
ChemSpider	2006673 (D-prolinol) N 555468 (L-prolinol) N
ECHA InfoCard	100.157.355
EC Number	245-605-2
PubChem CID	2724541 (D-prolinol) 640091 (L-prolinol)
UNII	H52Z235V6Y Y
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	101.149 g·mol−1
Appearance	Liquid
Density	1.036 g/mL (liquid)
Boiling point	74–76 °C (165–169 °F; 347–349 K) at 2 mmHg
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Irritant
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
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). N verify (what is YN ?) Infobox references

Preparation

Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydride.^[2][3] 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 reactions and the Michael reaction. ^[4][5]

See also

• Enantioselective synthesis

References

1. "D-Prolinol". pubchem.ncbi.nlm.nih.gov. Retrieved 27 December 2021.
2. Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. "Reduction of α-Amino Acids: L-Valinol". Organic Syntheses; Collected Volumes, vol. 7, p. 530.
3. Enders, D.; Fey, P.; Kipphardt, H. "(S)-(–)-1-Amino-2-Methoxymethylpyrrolidine (SAMP) and (R)-(+)-1-Amino-2-Methoxymethylpyrrolidine (RAMP), Versatile Chiral Auxiliaries". Organic Syntheses; Collected Volumes, vol. 8, p. 26.
4. Benjamin List (2002). "Proline-catalyzed asymmetric reactions". Tetrahedron. 58 (28): 5573–5590. doi:10.1016/S0040-4020(02)00516-1.
5. Shinichi Itsuno; Koichi Ito; Akira Hirao; 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.