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147-85-3 - L-Proline, 99% - H-Pro-OH - (S)-Pyrrolidine-2-carboxylic acid - A10199 - Alfa Aesar

A10199 L-Proline, 99%

CAS Number
147-85-3
Synonyms
H-Pro-OH
(S)-Pyrrolidine-2-carboxylic acid

Size Price ($) Quantity Availability
25g 22.09
100g 62.57
500g 208.85
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L-Proline, 99%

MDL
MFCD00064318
EINECS
205-702-2

Chemical Properties

Formula
C5H9NO2
Formula Weight
115.13
Melting point
ca 225° dec.
Density
1.36
Sensitivity
Hygroscopic
Solubility
Soluble in water and ethanol. Insoluble in ether, butanol and isopropanol.

Applications

L-Proline is used as asymmetric catalysts in organic synthesis and asymmetric aldol cyclization. It is involved in the Michael addition of dimethyl malonate to alfa-beta-unsaturated aldehydes. It is a precursor of hydroxyproline in collagen. It is an active component of collagen and involved in the proper functioning of joints and tendons. It finds uses in pharmaceutical, biotechnological applications due to its osmoprotectant property. Further, it is used with ninhydrin in the chromatography.

Notes

Hygroscopic. Incompatible with strong oxidizing agents.

Literature References

For use as a catalyst in an asymmetric aldol cyclization, see: Org. Synth. Coll., 7, 363 (1990). For reaction scheme, see 2-Methyl­cyclopentane-1,3-dione, A13936 . For use in a direct enantioselective crossed aldol reaction with aldehydes, see: J. Am. Chem. Soc., 124, 6798 (2002). For use as an organoctalyst in direct aldol reactions of ɑ-oxyaldehydes, as the first step in a two-step synthesis of carbohydrates, see: Angew. Chem. Int. Ed., 43, 2152 (2004). Mediates the enantioselective borane reduction of ketones to chiral alcohols with moderate to good ee: Monatsh. Chem., 131, 91 (2000). Also used to induce high ee in the ɑ-amination of aldehydes with Dibenzyl­ azodicarboxyl­ate, L19347 : J. Am. Chem. Soc., 124, 5656 (2002), or Diethyl­ azodicarboxyl­ate, L19348 : Angew. Chem. Int. Ed., 41, 1790 (2002).

For a review of the use of proline as a chiral catalyst, see: Synlett, 1675 (2001); Synlett, 1973 (2006).

For preparation from L-proline of the chiral hydrazone "SAMP", and enantioselective syntheses using the RAMP/ SAMP methodology, see: Org. Synth. Coll., 8, 26, 403 (1985).

For formation of a fused pyrrolidino-oxazolidinone, and use of the product in a synthesis of enantiopure ɑ-branched amino acids, see: Org. Synth. Coll., 9, 626 (1998); for reaction scheme, see Trimethyl­acetaldehyde, A15013 .

The Li salt has been used as a catalyst for the Michael addition of dimethyl malonate to ɑß-unsaturated aldehydes: J. Chem. Soc., Chem. Commun., 1088 (1991).

Sferrazza, A.; Triolo, A.; M Migneco, L.; Caminiti, R. Synthesis and Small and Wide Angle X-Ray Scattering Characterization of L-Proline Based Chiral Ionic Liquids. Curr. Org. Chem. 2015, 19 (1), 99-104.

Shimpi, M. R.; Childs, S. L.; Boström, D.; Velaga, S. P. New cocrystals of ezetimibe with l-proline and imidazole. CrystEngComm 2014, 16 (38), 8984-8993.

Other References

Merck
14,7780
Beilstein
80810
Harmonized Tariff Code
2933.99
TSCA
Yes
RTECS
TW3584000

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