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Chemical and Pharmaceutical Bulletin
Volumn 55, Issue 5, 2007, Pages 829-831
Preferential intramolecular ring closure of aminoalcohols with diethyl carbonate to oxazolidinones
Author keywords

aminoalanines; 5 Exo Trig; Aminoalcohol; Diethyl carbonate; Oxazolidinone; Ring closure
Indexed keywords

3 [(2 BENZYLIDENECYCLOHEXYL)METHYL] 4 (PIPERIDIN 1 YLMETHYL)OXAZOLIDIN 2 ONE; 3 [(2 HYDROXYCYCLOHEXYL)METHYL] 4 (PIPERIDIN 1 YLMETHYL)OXAZOLIDIN 2 ONE; 3 [[2 [HYDROXY(PHENYL)METHYL]CYCLOHEXYL]METHYL] 4 (PIPERIDIN 1 YLMETHYL)OXAZOLIDIN 2 ONE; AMINOALCOHOL; DIETHYL PYROCARBONATE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;
EID: 34248145324     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.55.829     Document Type: Article
Times cited : (5)
References (12)
  • 7
    • 0030039906 scopus 로고    scopus 로고
    • This compound was prepared from 2-hydroxycyclohexanecarboxylic acid and β-piperidinoalanine according to the procedure reported previously. 1,2) For the preparation of 2-hydroxycyclohexanecarboxylic acid, see de Raadt A, Griengl H, Petsch M, Plachota P, Schoo N, Weber H, Tetrahedron: Asymmetry, 7, 473-490 (1996, Compound (1, IR (KBr) cm-1: 3410. 1H-NMR (DMSO-d6) δ: 1.05, 1.64 (15H, m, Cyhx H-2, H-6 and Ppd H-3, H-5, 2.18, 2.38 (6H, m, CH2-1-Ppd and Ppd H-2, H-6, 2.42, 2.52 (1H, m, Cyhx-CHH, 2.56, 2.62 (1H, m, NHCHCH2N, 2.64, 2.71 (1H, m, Cyhx-CHH, 3.0, 3.3 (3H, br, OH x2, and NH, 3.31, 3.34 (2H, m, CH2OH, 3.79, 3.83 (1H, m, Cyhx H-1, FAB-MS (positive) m/z: 271 M+H, Anal. Calcd for C 15H30N2O2·0.4H2O: C, 64.90
    • 2O: C, 64.90; H, 11.18; N, 10.09. Found: C, 64.93; H, 11.17; N, 10.01.
  • 8
    • 0006747543 scopus 로고    scopus 로고
    • This compound was prepared from trans 2- benzoylcyclohexanecarboxylic acid and β-piperidinoalanine by the same method described previously.1,2) For the preparation of trans 2-benzoylcyclohexanecarboxylic acid, see Miyano S, Abe N, Fujisaki F, Sumoto K, Heterocycles, 26, 1813-1826 (1987, Compound (6, IR (KBr) cm-1: 3410, 3303. 1H-NMR (DMSO-d6, 70 °C) δ: 1.04, 1.75 (16H, m, Cyhx H-1, H-6, and Ppd H-3, H-5, 2.24, 2.82 (9H, m, Ppd H-2, H-6, CH2-Ppd, Cyhx-CH 2NHCHCH2 and CH2NHCHCH2N, 3.37 (2H, dd, J=5.5, 4.0 Hz, CH2OH, 3.8, 4.8 (2H, br, OH and OH or NH, 4.59 (1H, dd, J=13.0, 6.5 Hz, PhCHOH, 5.0, 6.0 (1H, br NH or OH, 7.25, 7.28 (5H, m, ArH, FAB-MS (positive) m/z: 361 M+H, Anal. Calcd for C22H36N 2O
    • 2O: C, 72.74; H, 10.07; N, 7.71. Found: C, 72.76; H, 10.16; N, 7.43.
  • 10
    • 34248220666 scopus 로고    scopus 로고
    • This compound was obtained from the reaction in the same manner described for (2, Starting 2-hydroxycyclohexanecarboxylic acid (cis, trans=ca. 3/1) was obtained by the method reported previously.7) The product 5 obtained in this experiment was an oily material. IR (KBr) cm-1: 3453 1691. 1H-NMR (DMSO-d6) δ: 1.21, 1.81 (6H, m, Cyhx H-5, HA-6, H-7 and H A-8, 1.61, 1.68 (1H, m, Cyhx HB-6, 1.74, 1.81 (1H, m, Cyhx HB-8, 1.93, 1.99 (1H, m, H-4a, 2.81 (3H, s, CH3, 2.90 (1H, dd, J=12.0, 2.5 Hz, H-4, 3.44 (1H, dd J=12.0, 5.5 Hz, H-4, 4.39, 4.41 (1H, m, H-8a, 13C-NMR (DMSO-d6) δ: 19.5, and 23.2 (C-7, 23.5, 23.9, 24.4, and 27.0 (C-5 and C-6, 29.2 and 30.8 (C-8, 31.4 and 35.8 (C-4a, 35.9 and 36.5 (CH3, 51.3 and 51.9 (C-4, 74.1 and 78.2 (C-8a, 152.5 (X2, CO, FAB-MS (positive) m/z
    • 2O: C, 62.88; H, 8.97; N, 8.15. Found: C, 62.85; H, 9.07; N, 7.87.
  • 11
    • 34248194527 scopus 로고    scopus 로고
    • -1 and an ion peak of 258 in negative FAB-MS, though the product is still as a labile mixture, are strongly indicating the formation of the target 7-membered compound (11).
    • -1 and an ion peak of 258 in negative FAB-MS, though the product is still as a labile mixture, are strongly indicating the formation of the target 7-membered compound (11).
  • 12
    • 34248169943 scopus 로고    scopus 로고
    • 9
    • 9)

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.