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)	DTXSID00988536 ;
	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
Main hazards	Irritant
R-phrases (outdated)	36/37/38
S-phrases (outdated)	26-36
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).

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 reactions 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.; Collective Volume, 7, p. 530
^ Enders, D.; Fey, P.; Kipphardt, H. "(S)-(–)-1-Amino-2-Methoxymethylpyrrolidine (SAMP) and (R)-(+)-1-Amino-2-Methoxymethylpyrrolidine (RAMP), Versatile Chiral Auxiliaries". Organic Syntheses.; Collective Volume, 8, p. 26
^ 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; 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.

[1] = Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. "Reduction of α-Amino Acids: L-Valinol". Organic Syntheses.; Collective Volume, 7, p. 530

[2] Enders, D.; Fey, P.; Kipphardt, H. "(S)-(–)-1-Amino-2-Methoxymethylpyrrolidine (SAMP) and (R)-(+)-1-Amino-2-Methoxymethylpyrrolidine (RAMP), Versatile Chiral Auxiliaries". Organic Syntheses.; Collective Volume, 8, p. 26

[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; 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.

[1]

[2]

[3]

[4]

Prolinol

Preparation

Use

See also

References