反应 #337976

反应方程式

oxazolidinone

(2R,5S)-5-Methyl-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one

diisopropylamine

oxazolidinone

(2R,5S)-2-Trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one

benzyl bromide

→

oxazolidinone

收率 32.0%

(2R,5R)-5-Benzyl-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one

收率 32.0%

反应条件

实验过程

(Wang et al. Synlett 1999, 1, 33). The reaction was carried out following a similar procedure to that described for the preparation of oxazolidinone 8 using n-butyllithium (1.31 M, 5.53 cm3, 7.2 mmol), diisopropylamine (1.01 cm3, 7.24 mmol), oxazolidinone 7 (1.18 g, 4.8 mmol) and benzyl bromide (1.72 cm3, 14.5 mmol) to afford oxazolidinone 11 (0.52 g, 32%) as a colourless crystalline solid: mp 75-77° C. (lit. Wang 72-77): δH (400 MHz; CDCl3) 1.32-1.55 (2H, m, Proγ-H2), 1.93-2.13 (2H, m, Proβ-H2), 2.58-2.65 (1H, m, Proδ-H2), 2.92 (1H, d, J 13.6, PhCHAHB), 2.98-3.03 (1H, m, Proδ-H2), 3.32 (1H, d, J 13.6, PhCHAHB), 4.99 (1H, s, NCH) and 7.21-7.35 (5H, m, PhH); δC (100 MHz; CDCl3) 24.8 (CH2, Proγ-C), 34.6 (CH2, Proβ-C), 41.6 (CH2, Proδ-C), 58.4 (CH2, PhCH2), 72.3 (quat., Proα-C), 100.6 (quat., CCl3), 102.8 (CH, NCH), 127.0 (CH, Ph), 128.2 (CH, Ph), 130.9 (CH, Ph), 135.5 (quat., Ph) and 176.6 (quat., C═O); m/z (EI+) 333.0081 [(M+H)+.C14H1435Cl3NO2 requires 333.0090], 335.0069 [(M+H)+.C14H1435Cl237ClNO2 requires 335.0061], 337.0014 [(M+H)+.C14H1435Cl37Cl2NO2 requires 337.0031] and 339.0009 [(M+H)+.C14H1437Cl3NO2 requires 339.0002].

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