An efficient asymmetric catalytic hydrogenation of 4-aryl coumarins, preparation of a key intermediate in the synthesis of a class of endothelin receptor antagonists

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3293-3296

  McGuire, Michael A ^a   Shilcrat, Susan C ^a   Sorenson, Edmund ^a  

^a Synthetic Chemistry Department   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 CARBOXYMETHOXY 4 METHOXYPHENYL) 1 (3,4 METHYLENEDIOXYPHENYL) 5 PROPOXY 2 INDANCARBOXYLIC ACID; COUMARIN DERIVATIVE; ENDOTHELIN RECEPTOR ANTAGONIST; ENRASENTAN;

ARTICLE; CATALYSIS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; ISOMER; REACTION ANALYSIS; RECEPTOR BLOCKING; STRUCTURE ANALYSIS;

EID: 0033597255     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00478-5     Document Type: Article

References (25)

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18. 3) δ 10.56, 22.60, 55.32, 69.53, 101.21, 106.75, 113.61, 114.49, 116.17, 119.59, 120.16, 129.65, 131.14, 141.40, 145.20, 154.34, 159.41, 160.80.
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20. 1H NMR for evidence of hydrogenation. The maleic acid procedure was repeated until no hydrogenation was observed.
21. 14. The progress of the hydrogenation and subsequent transformations could be followed by chromatographic analysis using an HP Hypersil ODS column (5 μ, 200 x 4.6 mm) with 60:40:0.1 acetonitrile:water:acetic acid as eluent at a flow rate of 1.0 mL/min and detection at 230 nm. The following retention times were observed: 2-16.3 min, 1-12.6 min, 3-4.6 min, 4-4.2 min.
22. 15. The enantiomeric excess of 1 was determined by chromatographic analysis on a Chiralpak AD column (Chiral Technologies) using 95:5 hexane:2-propanol as the mobile phase at a flow rate of 1.0 mL/min and detection at 275 nm. The retention times of 1 (S-isomer) and 1 (R-isomer) were 12.6 min and 11.4 min respectively.
23. 13 100 mL stainless steel autoclave was charged with 2 (7.75 g, 25.0 mmol), abs. methanol (69 mL), 4 N NaOH (12.5 mL, 50.0 mmol, 2 eq) and one of the following catalyst systems: a) [(S)-BINAP(p-cymene)(Cl) Ru]Cl (325 mg, 0.35 mmol, 1.4%);
24. 4 (36 mg, 0.05 mmol, 0.2%);
25. -1.