PREPARATION OF 1,2-AMINO ALCOHOLS
515
ArH). 13C NMR, d: 20.3, 44.9, 65.7, 122.4, 130.5, 132.4, 168.0. ESI-MS (m=z): 205.
Anal. calc. for C11H11NO3: C, 64.38; H, 5.40; N, 6.83. Found: C, 64.38; H, 5.42; N,
6.84.
2-[2-Hydroxy-2-(4-nitro-phenyl)-ethyl]-isoindole-1,3-dione
(3g)
(C16H12N2O5). Pale yellow solid, mp 166–168 ꢀC; IR (KBr) cmꢄ1: 1401.7, 1518.2,
1
1687.4, 1706.6, 2922.7, 3382.0. H NMR, d: 3.86 (dd, J ¼ 4.5 Hz & 14.1 Hz, 1H,
CHN), 4.01 (dd, J ¼ 8.0 Hz & 14.1 Hz, 1H, CHN), 5.16–5.20 (m, 1H, CHOH),
7.67 (d, J ¼ 8.6 Hz, 2H, ArH), 7.72–7.79 (m, 2H, ArH), 7.81–7.88 (m, 2H, ArH),
8.20 (d, J ¼ 8.7 Hz, 2H, ArH). 13C NMR, d: 45.7, 71.1, 123.7, 123.9, 127.4, 132.2,
134.5, 148.1, 150.2, 168.5. ESI-MS (m=z): 312. Anal. calc. for C16H12N2O5: C,
61.54; H, 3.87; N, 8.97. Found: C, 61.53; H, 3.85; N, 8.95.
2-(2-Hydroxy-cyclohexyl)-isoindole-1,3-dione (3h) (C14H15NO3). White
solid; mp 90–92 ꢀC; IR (KBr) cmꢄ1: 1450.8, 1467.3, 1653.1, 1707.1, 1772.1, 2862.3,
1
2937.9, 3447.8. H NMR, d: 1.21–1.42 (m, 4H, CH2’s), 1.68–1.83 (m, 2H, CH2),
2.13–2.24 (m, 2H, CH2), 3.97 (ddd, J ¼ 3.7, 10.1 & 12.4 Hz, CHN), 4.26–4.37 (m,
1H, CHOH), 7.67–7.74 (m, 2H, ArH), 7.78–7.85 (m, 2H, ArH). 13C NMR, d:
24.2, 25.1, 28.6, 34.6, 57.1, 68.6, 122.7, 131.7, 133.8, 169.5. ESI-MS (m=z): 245. Anal.
calc. for C14H15NO3: C, 68.56; H, 6.16; N, 5.71. Found: C, 68.59; H, 6.15; N, 5.73.
2-(1-Hydroxy-indan-2-yl)-isoindole-1,3-dione (3i) (C17H13NO3). Yellow
solid; mp 217–219 ꢀC; IR (KBr) cmꢄ1: 1468.3, 1711.6, 1771.1, 2854.1, 2925.9,
1
3491.4. H NMR, d: 3.12–3.24 (m, 1H, CH2), 3.95–4.08 (m, 1H, CH2), 5.11–5.18
(m, 2H, CHOH & CHN), 7.29–7.31 (m, 3H, ArH), 7.49–7.53 (m, 1H, ArH),
7.72–7.76 (m, 2H, ArH), 7.84–7.88 (m, 2H, ArH). 13C NMR, d: 32.7, 52.9, 76.2,
123.4, 124.9, 125.6, 127.5, 129.4, 131.9, 134.2, 140.2, 142.5, 169.6. ESI-MS (m=z):
279. Anal. calc. for C17H13NO3: C, 73.11; H, 4.69; N, 5.02. Found: C, 73.13; H,
4.65; N, 5.03.
2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-butyric acid ethyl
ester (3j) (C14H15NO5). syn-isomer. mp 58–60 ꢀC; IR (KBr) cmꢄ1: 1468.2, 1717.4,
1
1775.14, 2934.8, 2981.9, 3451.2. H NMR, d: 1.21–1.32 (m, 6H, CH3’s), 4.28 (q,
J ¼ 7.1 Hz, 2H, OCH2), 4.65–4.69 (m, 1H, CHOH), 4.99 (d, J ¼ 4.1 Hz, 1H,
CHN), 7.78–7.82 (m, 2H, ArH), 7.89–7.95 (m, 2H, ArH). 13C NMR, d: 14.5, 20.6,
59.7, 62.6, 67.1, 124.3, 130.8, 134.9, 167.7, 168.8. ESI-MS (m=z): 277. Anal. calc.
for C14H15NO5: C, 60.64; H, 5.45; N, 5.05. Found C, 60.63; H, 5.44; N, 5.01.
anti-isomer. oil; IR (KBr) cmꢄ1: 1468.2, 1717.4, 1775.14, 2934.8, 2981.9,
1
3451.2. H NMR, d: 1.21 (t, J ¼ 7.1 Hz, 3H, CH3CH2), 1.28 (d, J ¼ 6.4 Hz, 3H,
CH3CHOH), 4.28 (q, J ¼ 7.1 Hz, 2H, OCH2), 4.51–4.58 (m, 1H, CHOH), 4.71 (d,
J ¼ 6.5 Hz, 1H, CHN), 7.77–7.80 (m, 2H, ArH), 7.88–7.91 (m, 2H, ArH). 13C
NMR, d: 13.7, 19.3, 57.3, 61.9, 66.2, 123.5, 133.2, 134.5, 167.5, 168.5. ESI-MS
(m=z): 277. Anal. calc. for C14H15NO5: C, 60.64; H, 5.45; N, 5.05. Found: C,
60.63; H, 5.44; N, 5.01.
2-(2-Hydroxy-1-methyl-propyl)-isoindole-1,3-dione (3k) (C12H13NO3).
Semisolid; IR (KBr) cmꢄ1: 1467.7, 1614.1, 1707.0, 1773.7, 2935.2, 2977.4, 3446.7.
1H NMR, d: 1.20–1.27 (m, 3H, CH3CHOH), 1.41–1.48 (m, 3H, CH3CHN), 4.14
(m, 2H, CHOH & CHN), 7.28–7.78 (m, 2H, ArH), 7.82–7.87 (m, 2H, ArH). 13C