Ruthenium(III) Chloride–Catalyzed Ring Opening
2679
2-(2,6-Diisopropylphenyl)amino-2-phenyl-1-ethanol (3A):1H NMR
(300 MHz, CDCl3) d 1.18–1.27 (m, 12H), 3.04–3.27 (m, 4H), 4.95 (dd,
J ¼ 7.9, 3.6 Hz, 1H), 7.02–7.46 (m, 8H); 13C NMR (75 MHz, CDCl3) 24.4,
27.6, 58.5, 73.4, 123.6, 124.2, 125.9, 127.8, 128.7, 142.2, 142.3, 142.8;
EIMS m/z 297 (Mþ), 190, 175, 160, 107. Anal. calcd. for C20H27NO: C,
80.76; H, 9.15; N, 4.71. Found C, 80.79; H, 9.16; N, 4.73.
1
1-(4-Methylphenylamino)hexan-2-ol (4B): liquid; H NMR (300 MHz,
CDCl3) d 0.92 (t, J ¼ 6.9 Hz, 3H), 1.24–1.63 (m, 6H), 2.21 (s, 3H), 2.94 (dd,
J ¼ 12.4, 8.2 Hz, 1H), 3.26 (dd, J ¼ 12.4, 3.4 Hz, 1H), 3.82 (m, 1H), 6.62
(d, J ¼ 8 Hz, 2H), 6.89 (d, J ¼ 8 Hz, 2H); EIMS m/z 207 (Mþ), 190, 178,
135, 121, 107, 84, 57. Anal. calcd. for C12H19NO: C, 74.57; H, 9.19; N,
7.25. Found C, 74.56; H, 9.18; N, 7.21.
trans-2-(Phenylamino)cyclohexanol (5): mp 61–638C; lit.[6] 60–618C;
1H NMR (300 MHz, CDCl3) d 1.02–1.43 (m, 4 H), 1.71–1.82 (m, 2H),
2.11–2.23 (m, 2H), 2.82 (brs, 1 H, NH), 3.14 (ddd, J ¼ 4.1, 10.1, 10.2 Hz,
1H), 3.36 (ddd, J ¼ 4.2, 10.2, 10.4 Hz, 1H), 6.71–7.23 (m, 5H); 13C NMR
(75 MHz, CDCl3) d 24.3, 25.4, 31.7, 33.2, 60.3, 74.5, 114.5, 118.5, 129.4,
147.9; EIMS m/z 191 (Mþ), 174, 99, 82, 77, 41. Anal. calcd. for
C12H17NO: C, 75.35; H, 8.96; N, 7.32. Found C, 75.34; H, 8.98; N, 7.30.
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