219813-90-8

Upstream product

• 94104-32-2 ethyl 3-amino-3-(4-tolyl)propionate 
• 479065-00-4 (S)-3-amino-3-(4-methyl-phenyl)-propionic acid 
• 27835-00-3 ethyl (4-methylbenzoyl)acetate 
• 91108-05-3 ethyl 3-amino-3-(p-tolyl)-2-propenoate 

Downstream Products

• 219813-78-2 ethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetraacetoxy-5-(N-benzyloxycarbonyl-L-leucyl)aminohexanoyl]amino-3-(4-methylphenyl)propionate 
• 430474-95-6 (S)-3-[((2S,3R,4R,5R,6S)-6-Benzyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-3-p-tolyl-propionic acid ethyl ester 

Relevant academic research and scientific papers

Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane

Catalytic asymmetric reduction of N-unsubstituted β-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted β-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of β-aryl- and β-alkyl-substituted free β-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.

3-AMINO-3-ARYLPROPIONIC ACID n-ALKYL ESTERS, PROCESS FOR PRODUCTION THEREOF, AND PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-3-ARYLPROPIONIC ACIDS AND ESTERS OF THE ANTIPODES THERETO

The present invention is to provide an n-alkyl 3-amino-3-arylpropionate represented by the formula (I): wherein Ar1 represents an aryl group which may have a substituent(s), provided that a phenyl group and 4-methoxyphenyl group are excluded, R1 represents an n-propyl group or an n-butyl group, and a process for preparing the same, and its optically active compound and an optically active (S or R)-3-amino-3-arylpropionic acid represented by the formula (III-a): wherein Ar represents an aryl group which may have a substituent(s), and * represents an asymmetric carbon, and a process for preparing an optically active n-alkyl (R or S)-3-amino-3-arylpropionate represented by the formula (IV-a): wherein Ar and R1 have the same meanings as defined above, * represents an asymmetric carbon, provided that it has a reverse absolute configuration to the compound of the formula (III-a).