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Volumn 42, Issue 9, 2001, Pages 1765-1767

Preparation of enantiopure 4-arylmandelic acids via a Pd/C catalysed Suzuki coupling of enantiopure 4-bromomandelic acid

Author keywords

4 bromomandelic acid; Biaryl compounds; Palladium on carbon; Suzuki reaction

Indexed keywords

4 BROMOMANDELIC ACID; ALPHA METHYLBENZYLAMINE; CARBON; MANDELIC ACID DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

EID: 0035951951     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)02304-2     Document Type: Article
Times cited : (47)

References (15)
  • 13
    • 84992272733 scopus 로고    scopus 로고
    • The absolute stereochemistry of (7) was determined by single crystal X-ray of the least soluble salt
    • The absolute stereochemistry of (7) was determined by single crystal X-ray of the least soluble salt.
  • 14
    • 84992247215 scopus 로고    scopus 로고
    • General procedure: A solution of sodium carbonate (14.54 mmol, 1.25 equiv.) in water (6.25 ml) was added carefully to a stirred suspension of 4-bromomandelic acid (3) (11.63 mmol, 1.0 equiv.), arylboronic acid (12.79 mmol, 1.1 equiv.), 10% palladium on charcoal (0.23 mmol, 2 mol%) in 2-propanol (2.20 ml) and water (9.25 ml). The reaction was stirred at 62°C until complete, then it was cooled to ambient temperature and diluted with 70:15:1 2-propanol/water/2N NaOH solution (25 ml). The mixture was filtered and the catalyst was washed with the same solvent mixture (3×10 ml). The filtrate was diluted with water (25 ml) and acidified to ca. pH 2 with 2N HCl (14 ml). The 2-propanol was removed by vacuum distillation. The crystals that precipitated were filtered and washed with water (5×5 ml) (the pH of the washings was >pH 5), then dried under vacuum to yield the biaryl compound as a white solid
    • General procedure: A solution of sodium carbonate (14.54 mmol, 1.25 equiv.) in water (6.25 ml) was added carefully to a stirred suspension of 4-bromomandelic acid (3) (11.63 mmol, 1.0 equiv.), arylboronic acid (12.79 mmol, 1.1 equiv.), 10% palladium on charcoal (0.23 mmol, 2 mol%) in 2-propanol (2.20 ml) and water (9.25 ml). The reaction was stirred at 62°C until complete, then it was cooled to ambient temperature and diluted with 70:15:1 2-propanol/water/2N NaOH solution (25 ml). The mixture was filtered and the catalyst was washed with the same solvent mixture (3×10 ml). The filtrate was diluted with water (25 ml) and acidified to ca. pH 2 with 2N HCl (14 ml). The 2-propanol was removed by vacuum distillation. The crystals that precipitated were filtered and washed with water (5×5 ml) (the pH of the washings was >pH 5), then dried under vacuum to yield the biaryl compound as a white solid.
  • 15
    • 84992238204 scopus 로고    scopus 로고
    • All compounds were fully characterised
    • All compounds were fully characterised.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.