Resolution of racemic cis-1-amino-2-indanol by diastereomeric salt formation with (S)-2-phenylpropionic acid

Tetrahedron Asymmetry

Volumn 14, Issue 4, 2003, Pages 411-413

  Sakurai, Rumiko ^a   Sakai, Kenichi ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b Yamakawa Chemical Industry Co Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHOXYPHENYLACETIC ACID; ACID; ALCOHOL; DIBENZOYL DEXTRO TARTARIC ACID; HYDRATROPIC ACID; INDAN DERIVATIVE; INDINAVIR; MANDELIC ACID; SODIUM CHLORIDE; TARTARIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTALLIZATION; DIASTEREOISOMER; LIQUID; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0037458597     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00022-3     Document Type: Article

References (14)

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7. Senanayake C.H., DiMichele L.M., Liu J., Fredenburgh L.E., Ryan K.M., Roberts F.E., Larsen R.D., Verhoeven T.R., Reider P.J. Tertahedron Lett. 36:1995;7615.
8. Matsumoto, H.; Obara, Y. Jpn. Pat. Kokai 215,922, 1995; Chem. Abstr. 1996, 124, 175620.
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10. Luna A., Maestro A., Astorga C., Gotor V. Tetrahedron: Asymmetry. 10:1999;1967.
11. Askin, D.; Cianciosi, S. J.; Hoerrner, R. S. US Pat. 5,508,404, 1996 Hof, P. R. Eur. Pat. 890,571, 1998; Chem. Abstr. 1999, 130, 110062.
12. Refer to Ref. 8a (examples 10 and 11). Resolution yield=40% (de% of the salt has not been disclosed). The less-soluble salt was obtained as a methanol solvate. Enantiomerically pure cis-1 is obtained in 93% yield upon liberation of amine from the salt.
13. Resolution efficiency (E) has been calculated using the following equation: E=yield (%)×diastereomeric purity (% de)/100.
14. 3: C, 72.22; H, 7.07; N, 4.68. Found: C, 72.18; H, 7.11; N, 4.68%.