Positional isomerization of quinine and quinidine via rhodium on alumina catalysis: Practical one-step synthesis of Δ3,10-isoquinine and Δ3,10-isoquinidine

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5365-5368

  Portlock, David E ^a,c   Naskar, Dinabandhu ^b   West, Laura ^a   Seibel, William L ^a   Gu, Titan ^a   Krauss, Howard J ^a   Peng, X Sean ^a   Dybas, Paul M ^a   Soyke, Edward G ^a   Ashton, Stephen B ^a   Burton, Jonathan ^a  

^a PROCTER AND GAMBLE PHARMACEUTICALS   (United States)

^b Chembiotek Research International   (India)

^c WRIGHT STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKENE; ALUMINUM OXIDE; CINCHONA ALKALOID; DELTA 3,10 ISOQUINIDINE; DELTA 3,10 ISOQUININE; HYDROCHLORIC ACID; QUINIDINE; QUINIDINE DERIVATIVE; QUININE; QUININE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; ISOMER; ISOMERISM; SPECTROSCOPY;

CINCHONA; CINCHONA PUBESCENS;

EID: 0038684433     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01180-8     Document Type: Article

References (44)

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41. 3N:THF (3/95/0.2/0.2/2, v/v/v/v/v). At a flow rate of 1 mL/min, quinine was eluted at 11.0 min, the Z isomer at 16.5 min, and the E isomer at 17.8 min.
42. 3): δ 13.4 (1°, C-11), 23.5 (2°, C-7), 24.3 (2°, C-5), 25.3 (3°, C-4), 44.7 (2°, C-6), 56.4 (1°, C-11′), 57.5 (2°, C-2), 61.1 (3°, C-8), 66.9 (3°, C-9), 100.5 (3°, C-5′), 119.2 (3°, C-3′), 120.9 (3°, C-10), 122.7 (3°, C-7′), 132.0 (3°, C-8′), 147.9 (3°, C-2′).
43. 3, the result obtained at 2 h for the isomerization of quinidine ( 3 ) to a mixture of 6Z and 6E were 49, 17 and 34%, respectively, while after 24 h, 0% quinidine ( 3 ), 36% 6Z and 64% 6E were obtained.
44. +].