Abstract
The reaction of primary and secondary amines with epoxides in the presence of montmorillonite K10 clay, under solvent-free condtions and microwave irradiation affords high yields of β-amino alcohols.
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13.Selected Spectroscopic Data. —Compounds 3a–3g, 3j and 3k have been synthesized previously.3,4 The 1H NMR and 13C NMR spectra were recorded on a Broker AC80 instrument using CDC13 as solvent. Chemical shifts are in ppm relative to TMS. 3h: δH 1.28–1.51 (m, 4H), 1.98–2.52 (m, 6H), 3.01–3.18 (m, 2H), 3.42–3.63 (m, 1H), 3.63–3.90 (m, 3H), 4.70–5.12 (m, 2H), 5.34–5.88 (m, 1H). δC 23.46 (CH2), 54.34 (CH2), 59.18 (CH2), 67.94 (CH2), 72.24 (CH2), 72.94 (CH), 116.82 (CH2), 134.76 (CH). 3i: δH 2.12–2.75 (m, 6H), 3.31 (t, J =5.8 Hz, 4H), 3.41–4.06 (m, 6H), 4.85–5.38 (m, 2H), 5.52–6.11 (m, 1H). δC 53.88 (CH2), 61.53 (CH2), 66.29 (CH2), 66.75 (CH2), 77.23 (CH2), 77.33 (CH), 116.88 (CH2), 134.69 (CH). 31: δH 1.01 (d, J = 6.0 Hz, 6H), 1.61–1.88 (m, 4H), 2.27–2.76 (m, 6H), 3.34–3.98 (m, 3H), 4.51 (s, 1H). δC 21.92 (CH3), 23.99 (CH2), 54.20 (CH2), 59.10 (CH2), 68.10 (CH2), 70.91 (CH), 71.92 (CH). 3m: δH 1.20 (d, J = 6.1 Hz, 6H), 2.40–2.86 (m, 6H), 3.30–3.58 (m, 5H), 3.58–4.10 (m, 4H). δC 21.73 (CH3), 53.67 (CH2), 61.37 (CH2), 66.22 (CH2), 66.60 (CH2), 70.42 (CH), 71.75 (CH).