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1-Aminocyclopropanecarboxylic Acid
2879
Anal. calcd. for C23H16N2O4: C, 71.87; H, 4.20; N, 7.29. Found: C, 71.72;
H, 4.31; N, 7.39.
2e. White solid, yield 78%, m.p. 155 156ꢁC, Rf (hexane/ethyl acetate
4/1) 0.55. IR (KBr, ꢁ, cmꢂ1): 1803 (C¼O), 1628 (C¼N), 694 (Ar-H).
1H NMR (CDCl3, ꢀ, ppm): 8.0–6.4 (m, 13H, ArH), 4.03 (d, J ¼ 9.0 Hz,
1H, cyclopropyl), 3.77 (d, J ¼ 9.0 Hz, 1H, cyclopropyl). Anal. calcd. for
C21H15NO3: C, 76.58; H, 4.59; N, 4.25. Found: C, 76.51; H, 4.66; N, 4.30.
Syntheses of 3a–e
To a flask containing 40 mL of absolute methanol was added a little
piece of sodium, then to this solution was added 5 mmol of 2a–e under
stirring, the mixture was stirred for another 30 min (monitored by TLC,
hexane/ethyl acetate 3/1). After the reaction was finished, the methanol
was removed in vacuo. The solid was dissolved in ethyl acetate, then
washed by water, brine, dried over MgSO4 overnight. Filtered, the
solvent was removed in vacuo to provide a white solid of 3a–e.
3a. Yield 97%, m.p. 216–217ꢁC, Rf (hexane/ethyl acetate 3/1) 0.28.
IR (KBr, ꢁ, cmꢂ1): 3239 (N-H), 1732 (C¼O), 1645 (C¼O), 697 (Ar-H).
1H NMR (DMSO-d6, ꢀ, ppm): 9.07 (s, 1H, N-H), 7.7–7.1 (m, 15H, Ar-
H), 3.74 (d, J ¼ 9.0 Hz, 1H, cyclopropyl), 3.53 (d, J ¼ 8.5 Hz, 1H, cyclo-
propyl), 3.33 (s, 3H, CO2CH3). Anal. calcd. for C24H21NO3: C, 77.61; H,
5.70; N, 3.77. Found: C, 77.55; H, 5.78; N, 3.82.
3b. Yield 99%, m.p. 169–171ꢁC, Rf (hexane/ethyl acetate 3/1) 0.20.
IR (KBr, ꢁ, cmꢂ1): 3274 (N-H), 1738 (C¼O), 1634 (C¼O), 697 (Ar-H).
1H NMR (CDCl3, ꢀ, ppm): 7.7–6.9 (m, 14H, Ar-H), 6.15 (s, 1H, N-H),
3.83 (s, 3H, OCH3), 3.71 (d, J ¼ 9.0 Hz, 1H, cyclopropyl), 3.48 (s, 3H,
OCH3), 3.44 (d, J ¼ 9.0 Hz, 1H, cyclopropyl). Anal. calcd. for
C25H23NO4: C, 74.49; H, 5.77; N, 3.49. Found: C, 74.45; H, 5.80; N, 3.53.
3c. Yield 98%, m.p. 183ꢁC, Rf (hexane/ethyl acetate 3/1) 0.29. IR
(KBr, ꢁ, cmꢂ1): 3237 (N-H), 1739 (C¼O), 1632 (C¼O), 698 (Ar-H).
1H NMR (CDCl3, ꢀ, ppm): 7.6–7.3 (m, 14H, Ar-H), 6.20 (s, 1H, N-H),
3.74 (d, J ¼ 8.5 Hz, 1H, cyclopropyl), 3.48 (s, 3H, OCH3), 3.46
(d, J ¼ 9.0 Hz, 1H, cyclopropyl). Anal. calcd. for C24H20NO3Cl: C,
71.02; H, 4.97; N, 3.45. Found: C, 70.92; H, 5.01; N, 3.49.
3d. Yield 92%, m.p. 209ꢁC, Rf (hexane/ethyl acetate 3/1) 0.18. IR
(KBr, ꢁ, cmꢂ1): 3249 (N-H), 1741 (C¼O), 1634 (C¼O), 700 (Ar-H).
1H NMR (DMSO-d6, ꢀ, ppm): 9.28 (s, 1H, N-H), 8.1–7.3 (m, 14H,
Ar-H), 3.93 (d, J ¼ 8.5 Hz, 1H, cyclopropyl), 3.69 (d, J ¼ 8.5 Hz, 1H,
cyclopropyl), 3.35 (s, 3H, OCH3). Anal. calcd. for C24H20N2O5:
C, 69.22 ; H, 4.84; N, 6.73. Found: C, 69.31; H, 4.80; N, 6.81.