An alternative approach to achieve enantiopure (3S)-4-benzyl-3-(4- fluorophenyl)morpholin-2-one: A key intermediate of aprepitant, an NK1 receptor antagonist

Organic Process Research and Development

Volumn 11, Issue 3, 2007, Pages 455-457

  Kolla, Naveenkumar ^a   Elati, Chandrashekar R ^a   Arunagiri, Muthulingam ^a   Gangula, Srinivas ^a   Vankawala, Pravinchandra J ^a   Anjaneyulu, Yerremilli ^b   Bhattacharya, Apurba ^a   Venkatraman, Sundaram ^a   Mathad, Vijayavitthal T ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

^b JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 39049150436     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op700030d     Document Type: Article

References (16)

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7. http://www.rxlist.com/cgi/generic3/emend.htm.
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10. Todd, D. N.; Mahadevan, B. U.S. Patent 6,177,564, 2001.
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12. Zhao, M. M.; McNamara, J. M.; Ho, G.-J.; Emerson, K. M.; Song, Z. J.; Tschaen, D. M.; Brands, K. M. J.; Dolling, U.-H.; Grabowski, E. J. J.; Reider, P. J.; Cottrell, I. F.; Ashwood, M. S.; Bishop, B. C. J. Org. Chem. 2002, 67, 6743.
13. Kozma, D. CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation; CRC Press: Boca Raton, FL, 2002.
14. On the other hand, the diastereomeric salt (-)-9·(-)-DPTTA is precipitated in methanol to optionally access (-)-9.
15. Enamiopurity of (S)-(+)-9 was determined by chiral HPLC analysis with Chiralpak ODH, 5.0 μm, 250 mm × 4.6 mm; mobile phase: n-hexane, ethanol, and diethylamine in the ratio of 95:5:0.01 (v/v); 1.0 mL/min; 210 nm. The retention times of (S)-(+)-9 and (R)-(-)-9 were around 33.23 and 28.14 min, respectively.
16. Enantiopurity of (S)-(+)-2 was determined by chiral HPLC analysis with Chiralpak ODH, 5.0 μm, 250 mm × 4.6 mm; mobile phase: n-hexane, ethanol, and diethylamine in the ratio of 95:5:0.01 (v/v); 0.8 mL/min; 210 nm. The retention times of (S)-(+)-2 and (R)-(-)-2 were around 23 and 19 min, respectively.