References
- Massiot , G. and Delaude , C. 1986 . The Alkaloids , Edited by: Manske , R. H. F. Vol. 27 , New York : Academic Press . Chapter 3
- Padwa , A. and Norman , B. H. 1990 . J. Org. Chem. , 55 : 4081
- Wang , C. J. and Wuonola , M. A. 1990 . Org. Prep. Rep. , : 447
- Jorids , U. , Sauter , F. , Siddiqi , S. M. , Kuenburg , B. and Bhattacharya , K. 1990 . Synthesis , : 925
- Lee , J. W. , Son , H. J. , Jung , Y. E. and Lee , J. H. Synlett , submitted.
- Lee , J. W. , Son , H. J. and Choi , M. J. 1994 . Korean J. Med. Chem. , 4 : 119
- Lee , J. W. , Jung , Y. E. , Son , H. J. , Yoon , G. J. , Kong , M. S. and Kim , D. Y. Synth. Commum , submitted
- 3-Thiosubstituted propylamines were prepared by the reaction of 3-chloropropyl amine and the appropriate thiols in water in the presence of NaOH
- Lee , J. W. , Lee , J. H. , Son , H. J. , Choi , Y. K. , Yoon , G. J. and Park , M. H. Bull. Kor. Chem. Soc. , submitted
- Agami , C. , Couty , F. , Hamon , L. and Venier , O. 1993 . Tetrahedron Lett. , 34 : 4509
- A typical procedure is as follows: To a stirred solution of 2b (2.3 g, 7.92 mmol) in 35ml of pyridine was added TsCl (4.5 g, 23.6 mmol) at 0°C. The reaction mixture was stirred at room temperature for 1h. Pyridine was evaporated, treated with EtOAc (100 ml), and washed with H2O (50 ml × 2). The EtOAc layer was concentrated, treated with THF (120 ml), and added slowly 1N NaOH (80 ml). The mixture was stirred for 30min, extracted with EtOAc, and washed with brine. The organic layer was dried and concentrated. The residue was crystallized from methanol to give 3 g (63.3 %) of 3b. 3a: mp 136∼138°C; 6HNMR (CDCl3) δ 1.42(s, 9H), 1.60∼1.96(m, 2H), 2.41(s, 3H), 2.44(s, 3H), 2.79(t, J=6.6Hz, 2H), 2.99∼3.43(m, 4H), 3.52∼3.83(m, 2H), 4.21∼4.50(m, 1H), 4.78∼5.04(m, 1H), 7.20∼7.36(m, 9H), 7.61∼7.76(m, 4H). 3b: mp 102∼104°C; 1HNMR (CDCl3) δ 1.42(s, 9H), 1.61∼1.95(m, 2H), 2.06(s, 3H), 2.38(t, J=6.5Hz, 2H), 2.43(s, 3H), 2.46(s, 3H), 2.91∼3.32(m, 4H), 3.45∼3.82(m, 2H), 4.26∼4.55(m, 1H), 4.87∼5.12(m, 1H), 7.24∼7.40(m, 4H), 7.65∼7.80(m, 4H)
- A typical procedure is as follows: To a stirred solution of 4c (2.51 g, 4.08 mmol) in 40 ml of THF was added dropwise 4.94ml (4.5 mmol) of t-BuOK (1M in THF) at -10°C. After stirring for 30min at -10°C, the reaction mixture was quenched with saturated ammonium chloride solution(50 ml) and extracted with chloroform. The organic layer was washed with brine, dried, and concentrated. The residue was crystallized from ethyl ether: n-hexane system to give 1.68 g (93.3%) of 5c. 5a: 1HNMR (CDCl3) δ 1.48(s, 9H), 1.71∼2.27(m, 2H), 2.42(s, 3H), 2.59∼3.23(m, 2H), 3.31∼3.64(m, 2H), 4.06(m, 4H), 5.20∼5.33(m, 1H), 7.29(d, J=8.3Hz, 2H), 7.43∼7.67(m, 7H). 5b: mp 93∼95°C; 1HNMR (CDCl3) δ 1.48(s, 9H), 1.87∼2.22(m, 2H), 2.42(s, 3H), 3.06∼3.30(m, 2H), 3.52(t, J=6.6Hz, 2H), 4.06(m, 4H), 5.22∼5.37(m, 1H), 7.29(d, J=8.3Hz, 2H), 7.56∼7.78(m, 5H), 7.87∼7.99(m, 2H). 5c: mp 120∼122°C; 1HNMR (CDCl3) δ 1.47(s, 9H), 1.93∼2.25(m, 2H), 2.43(s, 3H), 2.60(s, 3H), 2.70∼2.97(m, 2H), 3.50∼3.67(m, 2H), 4.12(m, 4H), 5.31∼5.41(m, 1H), 7.31(d, J=8.4Hz, 2H), 7.64(d, J=8.4Hz, 2H). 5d: mp 139∼141°C; 1HNMR (CDCl3) δ 1.47(s, 9H), 1.97∼2.33(m, 2H), 2.44(s, 3H), 2.96(s, 3H), 3.07∼3.26(m, 2H), 3.58(t, J=6.3Hz, 2H), 4.13(m, 4H), 5.33∼5.43(m, 1H), 7.32(d, J=8.4Hz, 2H), 7.64(d, J=8.4Hz, 2H)
- Claes , P. , Vlietinck , A. , Roets , E. and Vanderhaeghe , H. 1973 . J. Chem. Soc., Perkin. , I : 932
- 6: 1HNMR (CDCI3) δ 1.47(s, 9H), 1.69∼1.96(mY 2H), 2.09(s, 3H), 2.43(s, 3H), 2.32∼2.63(mY 2 3, 3.51(tY J=6.6Hz, 2H), 4.11(mY 4H), 5.29∼5.41(mY lH), 7.30(d, J=8.4HzY 2H), 7.66(d, J=8.4HzY 2H); Mass(70 ev), m/z(%) 57(40.7), 171(58.7), 215(100), 426(1.5, M+).