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Volumn , Issue 5, 2009, Pages 0779-0782

A highly efficient conversion of primary or secondary alcohols into fluorides with n-perfluorobutanesulfonyl fluoride-tetrabutylammonium triphenyldifluorosilicate

Author keywords

Elimination; Fluorination; PBSF; Stereoselectivity; TBAT

Indexed keywords


EID: 62349129313     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087931     Document Type: Article
Times cited : (17)

References (14)
  • 5
    • 62349131339 scopus 로고    scopus 로고
    • These side products were determined by LC-MS or other means
    • These side products were determined by LC-MS or other means. For details, please see ref. 12.
    • For details, please
  • 6
    • 62349097424 scopus 로고    scopus 로고
    • Typical Procedure The alcohol 4, TBAT in the amount indicated, base, and solvent (8 mL/mmol) were added in turn at the temperature indicated. Then PBSF (2.2 equiv) was introduced and stirring was continued for the time given. The final reaction mixture was directly assayed by HPLC or LC-MS, and the calculation of HPLC data gave conversion, dr value, and ratio of fluorination product/elimination product in the mixture. The final reaction mixture was then concentrated under reduced pressure and purified by flash chromatography (eluent: PE to PE-acetone) to give (2S,4S, 3a, and a mixture of 5 and 6 (not separated, 2S,4S)-Methyl 4-Fluoro-1-(4- methylphenylsulfonyl)-pyrrolidine-2-carboxylate, 2S,4S)-3a] White crystals; Rf, 0.44 (PE-acetone, 70:30, mp 100-103°C; [α]D24 -60 (c 0.94, EtOAc, IR KBr, n, 3006, 29
    • 4S + Na: 304.0619; found: 304.0612.
  • 11
    • 62349107323 scopus 로고    scopus 로고
    • Typical Procedure for the Synthesis of (2S,4S)-Methyl 1-[4,4-Bis(3-methyl-2-thienyl)-3-buten-1-yl]-4- fluoropyrrolidine-2-carboxylate (3g) To a mixture of alcohol 1g (1 equiv) and TBAT (0.8 equiv, i-Pr2NEt (2.5 equiv) and toluene (8 mL per mmol of alcohol) were added in turns at r.t. The resulting mixture was stirred, and then PBSF (2.2 equiv) was introduced. The stirring was continued until TLC revealed complete conversion. The reaction mixture was concentrated under reduced pressure. The residual was mixed with a little bit of silica gel, airdried, and finally purified by flash chromatography (SiO2, 300-400 mesh; eluent: PE to PE-acetone) to give 3g as a yellow oil; [α]D24 -31 (c 0.89, EtOAc, IR (NaCl, n, 3104, 3060, 2952, 2843, 1748, 1733, 1435, 1200, 1174, 715 cm-1. 1H NMR (600 MHz, CDCl3, δ, 2.00 (s, 3 H, 2.03 s, 3 H
    • 2 + 1): 394.1310; found: 394.1316.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.