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Volumn 67, Issue 24, 2002, Pages 8688-8691

A practical and improved synthesis of (3S,5S)-3-[(tert-butyloxycarbonyl)methyl]-5- [(methanesulfonyloxy)methyl]-2-pyrrolidinone

Author keywords

[No Author keywords available]

Indexed keywords

DECARBOXYLATION;

EID: 0037195660     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020433f     Document Type: Article
Times cited : (18)

References (34)
  • 3
    • 2242483996 scopus 로고    scopus 로고
    • note
    • tert-Butyl ester functionality was specifically chosen for the crystallinity of the intermediates in the synthesis.
  • 4
    • 2242464219 scopus 로고    scopus 로고
    • note
    • The trans/cis stereochemical notation refers to the C3 and C5 positions.
  • 20
    • 2242437417 scopus 로고    scopus 로고
    • note
    • Acetal 5b is too labile under decarboxylation conditions. For 5c and 5d, isobutyraldehyde (bp 63 °C) and pivalaldehyde (bp 74 °C) can be conveniently removed by evaporation either in protection or deprotection steps, but they are more difficult to deprotect under mild conditions.
  • 27
    • 2242423853 scopus 로고    scopus 로고
    • note
    • 1H NMR integration in which the C-4 protons are characteristic for the trans isomer (δ 3.41 ppm) and the cis isomer (δ 3.59 ppm).
  • 29
    • 2242450815 scopus 로고    scopus 로고
    • note
    • The C-O bond was cleaved and the corresponding N-benzyl product was obtained.
  • 32
    • 2242478684 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of crude 11 revealed that ∼5% starting material 10 remained intact as well as some unidentified side-products.
  • 33
    • 2242456167 scopus 로고    scopus 로고
    • note
    • 1H NMR of the corresponding Mosher ester of 11 derived from both (5S)- and (5R)-2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.