Prolinol

Structural formula
	( S ) -prolinol
General
Surname	Prolinol
other names	( S ) -2-hydroxymethylpyrrolidine; ( S ) -2-pyrrolidinemethanol;
Molecular formula	C 5 H 11 NO
External identifiers / databases
EC number	629-147-4
ECHA InfoCard	100.157.355
PubChem	2724541
ChemSpider	2006673
Wikidata	Q7249621
properties
Molar mass	101.15 g mol −1
Physical state	liquid
density	1.025 g cm −3
boiling point	74-76 ° C (2 mm Hg )
Refractive index	1.4849
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Prolinol , more precisely ( S ) -prolinol , is a chemical compound from the group of chiral 1,2-amino alcohols and pyrrolidines . The enantiomeric ( R ) -prolinol and the racemic ( RS ) -prolinol are of little importance.

Whenever the term prolinol is mentioned in this article or in the scientific literature without a prefix , it always means ( S ) -prolinol, which has the same configuration as the natural amino acid ( S ) -proline (synonym: L -proline).

Extraction and presentation

( S ) -Prolinol is made by reducing ( S ) -proline with lithium aluminum hydride .

use

Prolinol is used as a chiral building block for the synthesis of z. B. Dibromphakellstatin is used.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet (R) - (-) - 2-pyrrolidinemethanol, 99% from Sigma-Aldrich , accessed on August 18, 2015 ( PDF ).
↑ ^a ^b Data sheet (S) - (+) - 2-pyrrolidinemethanol, 97% from Sigma-Aldrich , accessed on August 18, 2015 ( PDF ).
^ DA Dickman, AI Meyers, GA Smith, RE Gawley: REDUCTION OF α-AMINO ACIDS: L-VALINOL In: Organic Syntheses . 63, 1985, p. 136, doi : 10.15227 / orgsyn.063.0136 ; Coll. Vol. 7, 1990, p. 530 ( PDF ).
↑ Delphine EN Jacquot, Michael Zöllinger, Thomas Lindel: Total synthesis of the marine natural product rac-Dibromphakellstatin . In: Angewandte Chemie . tape 117 , no. January 15 , 2005, doi : 10.1002 / anie.200462252 .

[Sigma1-1] ↑ ^a ^b ^c ^d ^e data sheet (R) - (-) - 2-pyrrolidinemethanol, 99% from Sigma-Aldrich , accessed on August 18, 2015 ( PDF ).

[Sigma2-2] Data sheet (S) - (+) - 2-pyrrolidinemethanol, 97% from Sigma-Aldrich , accessed on August 18, 2015 ( PDF ).

[3] DA Dickman, AI Meyers, GA Smith, RE Gawley: REDUCTION OF α-AMINO ACIDS: L-VALINOL In: Organic Syntheses . 63, 1985, p. 136, doi : 10.15227 / orgsyn.063.0136 ; Coll. Vol. 7, 1990, p. 530 ( PDF ).

[4] Delphine EN Jacquot, Michael Zöllinger, Thomas Lindel: Total synthesis of the marine natural product rac-Dibromphakellstatin . In: Angewandte Chemie . tape 117 , no. January 15 , 2005, doi : 10.1002 / anie.200462252 .