تفاعل #337974

معادلة التفاعل

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

iodoethane

→

oxazolidinone

المردود 46.0%

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

المردود 46.0%

ظروف التفاعل

الإجراء التجريبي

The reaction was carried out following a similar procedure to that described for the preparation of oxazolidinone 8 using n-butyllithium (1.31 M, 28.3 cm3, 37.1 mmol), diisopropylamine (5.2 cm3, 37.1 mmol), oxazolidinone 7 (6.0 g, 24.7 mmol) and iodoethane (5.9 cm3, 73.8 mmol) to afford oxazolidinone 9 (3.05 g, 46%) as a light red oil that solidified on standing to a pale brown solid: mp 76-77° C.: [α]D +18.5 (c 0.25 in CHCl3): δH (300 MHz; CDCl3) 1.04 (3 H, t, J 7.5, CH3), 1.60-1.80 (1H, m, CHAHBCH3), 1.72-1.99 (4H, m, CHAHBCH3, Proβ-HAHB and Proγ-H2), 2.20-2.30 (1H, m, Proβ-HAHB), 3.22-3.29 (2H, m, Proδ-H2) and 5.00 (1 H, s, NCH); δC (75 MHz; CDCl3) 8.4 (CH3, CH3), 25.5 (CH2, CH2CH3), 30.9 (CH2, Proγ-C), 35.6 (CH2, Proβ-C), 58.6 (CH2, Proδ-C), 72.5 (quat., Proα-C), 100.9 [quat., C(Cl3)], 102.5 (CH, NCH) and 176.9 (quat., CO); m/z (EI+) 272.0014 (MH+.C9H1335ClN3O2 requires 272.0012).

المصدر