Case study of a γ-butyrolactone alkylation with 1,3-dimethyl-2-imidazolidinone as a promoter

Organic Process Research and Development

Volumn 5, Issue 6, 2001, Pages 609-611

  Li, B ^a   Buzon, Richard A ^a   Castaldi, Michael J ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035565690     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op010224h     Document Type: Article

References (25)

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17. Preparation of 2-benzyl-3-hydroxy-γ-butyrolactone on millimole scale was reported using DMI as a cosolvent. In this reaction, benzyl bromide (1.0 equiv) was used an limiting reagent (DMI, 14 equiv, and the γ-butyrolactone, 5.2 equiv): Higamie, K.; Furukawa, Y.; Katsumura, S.; Takehira, Y. Jpn. Kokai Tokkyo Koho, JP 11189589, 1999.
18. Brun, E. M.; Gil, S.; Parra, M. Syn. Lett. 2001, 1, 156; Tetrahedron Asymmetry, 2001, 12, 915.
19. Brun, E. M.; Gil, S.; Parra, M. Syn. Lett. 2001, 1, 156; Tetrahedron Asymmetry, 2001, 12, 915.
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22. In the presence of DMI, the reaction time needed was less than 2 min, 2 h or longer was needed in the absence of DMI.
23. By HPLC area, monitored at 210 nm wavelength.
24. 3, 400 MHz) δ 17.78, 25.68, 28.08, 29.27, 29.33, 38.73, 38.92, 54.32, 78.41, 79.91, 113.43, 113.64, 115.98, 116.18, 119.42, 124.86, 124.88, 129.92, 130.00, 135.21, 139.70, 139.78, 155.79, 161.53, 163.98, 179.38.
25. Enolates were generated at -78 °C with 1.0 M LHMDS (1.05 equiv) solution in THF as base. DMI (1.2 equiv) was added prior to the addition of the alkyl halide (1.10 equiv). The reaction temperature shown was maintained during the alkyl halide addition. Yields and diastereomer ratios were based on HPLC analysis at 210 nm.