1992 Bull. Korean Chem. Soc. 2014, Vol. 35, No. 7
Laleh Faraji et al.
−1
129.6, 130.2, 132.6. FT-IR (KBr, cm ) 3403, 2956, 2859,
22.4, 23.2, 24.9, 31.7, 38.3, 39.8, 48.3, 58.7, 60.9, 63.3,
+
−1
1564, 1364, 1144, 1056, 759, 701. MS (m/z) = 250 (M );
Anal. calcd for C15H26N2O: C 71.95, H 10.47, N 11.19;
126.3, 128.6, 129.2, 138.8. FT-IR (KBr, cm ) 3367, 2956,
2927, 2860, 1564, 1139, 1040, 744, 700. MS (m/z) = 264
(M ); Anal. calcd for C16H28N2O: C 72.68, H 10.67, N 10.59;
+
found C 71.99, H 10.44, N 11.26.
(S)-2-(((S)-2-(Methylamino)-2-phenylethyl)amino)-3-
phenylpropan-1-ol (1d): Light yellow iol (232 mg, 82%).
found C 72.75, H 10.71, N 10.54.
(S)-2-(((S)-2-(Benzylamino)-4-methylpentyl)amino)-3-
phenylpropan-1-ol (1i): Light yellow oil (275 mg, 81%).
[α]2D0 = +12.l5 (c = 4, CH2Cl2). H NMR (300 MHz, CDCl3)
1
[α]2D0 = +22 (c = 0.2, CH2Cl2). H NMR (300 MHz, CDCl3)
1
δH 2.25 (s, 3H), 2.68 (t, 2H), 2.81 (d, 2H), 2.93 (m, 4H),
3.31-3.37 (dd, 1H), 3.55-3.59 (m, 2H), 7.23-7.32 (m, 10H).
δH 0.88 (t, J = 6.6 Hz, 6H), 1.10-1.21 (m, 1H), 1.31-1.46 (m,
1H), 1.51-1.68 (m, 1H), 2.41-2.49 (m, 1H), 2.66-2.76 (m,
13
C NMR (75.46 MHz, CDCl3) δC 34.0, 38.1, 52.6, 63.1,
2
3
64.8, 65.0, 127.0, 127.2, 127.5, 127.6, 128.1, 128.5, 140.7,
4H), 2.83-2.87 (m, 1H), 3.33-3.38 (dd, J = 10.7 Hz, J = 5.6
−1
2
3
141.2. FT-IR (KBr, cm ) 3389, 2958, 2920, 2851, 1262,
Hz, 1H), 3.59-3.63 (dd, J = 10.7 Hz, J = 3.8 Hz, 1H), 3.63-
3.72 (m, 2H), 7.19-7.35 (m, 10H). C NMR (75.46 MHz,
+
13
1035, 800, 701. MS (m/z) = 284 (M ); Anal. calcd for
C18H24N2O: C 76.02, H 8.51, N 9.85; found C 76.11, H 8.59,
CDCl3) δC 18.5, 18.9, 20.7, 37.8, 38.5, 45.8, 46.6, 50.1, 60.4,
62.5, 122.7, 123.0, 133.2,124.0, 124.3, 124.9, 136.1, 136.7.
N 9.79.
−1
(S)-2-(((S)-2-(Methylamino)-3-phenylpropyl)amino)-3-
phenylpropan-1-ol (1e): Light yellow oil (238 mg, 80%).
FT-IR (KBr, cm ) 3336, 3031, 2998, 2945, 1458, 1035, 742,
+
700. MS (m/z) = 340 (M ); Anal. calcd for C22H32N2O: C
[α]2D0 = +230.76 (c = 0.23, CH2Cl2). H NMR (300 MHz,
77.60, H 9.47, N 8.23; found C 77.65, H 9.45, N 8.28.
(S)-2-(((S)-2-(Benzylamino)-4-methylpentyl)amino)-2-
phenylethanol (1j): Light yellow oil (283 mg, 87%). [α]D20
1
CDCl3) δH 2.19 (d, J = 6 Hz, 2H), 2.37 (s, 3H), 2.55-2.93 (m,
2
3
7H), 3.31-3.37 (dd, J = 10.5 Hz, J = 6.5 Hz, 1H), 3.56-3.60
2
3
13
1
(dd, J = 10.5 Hz, J = 3.1 Hz, 1H), 7.09-7.29 (m, 10H). C
NMR (75.46 MHz, CDCl3) δC 28.6, 29.3, 33.8, 53.5, 61.5,
64.7, 65.0, 126.9, 127.2, 127.3, 127.5, 128.4, 128.6, 141.3,
= +56.07 (c = 0.9, CH2Cl2). H NMR (300 MHz, CDCl3) δH
0.85-0.90 (dd, 6H), 1.10-1.23 (m, 1H), 1.32-1.48 (m, 1H),
2
1.48-1.64 (m, 1H), 2.12-2.34 (br s, 3H), 2.38-2.45 (dd, J =
11.7 Hz, J = 7.7 Hz, 1H), 2.56-2.61 (dd, J = 11.7 Hz, J =
3.6 Hz, 1H), 2.63-2.78 (m, 2H), 3.49-3.63 (m, 1H), 3.63-
−1
3
2
3
141.4. FT-IR (KBr, cm ) 3337, 3025, 2932, 2846, 1564,
+
1135, 1033, 744, 701. MS (m/z) = 298 (M ); Anal. calcd for
C19H26N2O: C 76.47, H 8.78, N 9.39; found C 76.57, H 8.85,
13
3.82 (m, 3H), 7.19-7.36 (m, 10H). C NMR (75.46 MHz,
N 9.36.
CDCl3) δC 18.4, 18.9, 20.7, 37.9, 45.9, 46.5, 50.2, 60.3, 62.6,
123.0, 133.2, 124.0, 124.2, 124.3, 124.9, 136.1, 136.7. FT-IR
(S)-3-Methyl-2-(((S)-3-methyl-2-(methylamino)butyl)-
amino)butan-1-ol (1f): Light yellow oil (158 mg, 78%).
−1
(KBr, cm ) 3350, 3016, 2958, 1458, 1374, 1208, 1031, 752,
[α]2D0 = –107 (c = 0.23, CH2Cl2). H NMR (300 MHz, CDCl3)
700. MS (m/z) = 326 (M ); Anal. calcd for C21H30N2O: C
1
+
δH 0.85 (t, J = 5.8 Hz, 6H), 0.92 (d, J = 6.4 Hz, 6H), 1.67-
1.79 (m, 1H) 1.79-1.89 (m, 1H), 2.33 (br s, 1H), 2.37 (s,
3H), 2.49 (t, 1H), 2.71 (br d, 1H), 3.35 (t, 1H), 3.58-3.61 (m,
77.26, H 9.26, N 8.58; found C 77.33, H 9.29, N 8.51.
(S)-2-(((S)-2-(Benzylamino)-4-methylpentyl)amino)-4-
methylpentan-1-ol (1k): Colorless oil (269 mg, 88%). [α]D20
13
1
4H). C NMR (75.46 MHz, CDCl3) δC 18.8, 18.9, 19.5,
= −44 (c = 0.5, CH2Cl2). H NMR (300 MHz, CDCl3) δH
19.6, 29.3, 29.6, 33.9, 53.9, 61.6, 64.7, 65.4. FT-IR (KBr,
0.89 (d, J = 5.8 Hz, 12H), 1.10-1.30 (m, 4H), 1.56-1.78 (m,
2H), 2.39-2.75 (m, 6H), 3.20-3.30 (m, 1H), 3.54-3.58 (dd,
−1
+
cm ) 3359, 2959, 2874, 1567, 1048. MS (m/z) = 202 (M );
Anal. calcd for C11H26N2O: C 65.30, H 12.95, N 13.84;
found C 65.28, H 12.98, N 13.90.
13
1H), 3.74-3.78 (dd, 2H), 7.23-7.31 (m, 5H). C NMR (75.46
MHz, CDCl3) δC 18.4, 18.5, 18.7, 18.9, 20.6, 20.7, 35.6, 35.8,
37.9, 51.6, 50.7, 60.4, 62.3, 123.0, 133.2,124.0, 124.2. FT-IR
(S)-4-Methyl-2-(((S)-4-methyl-2-(methylamino)pentyl)
amino)pentan-1-ol (1g): Light yellow oil (193 mg, 84%).
−1
(KBr, cm ) 3336, 3025, 2961, 2859, 1367, 1161, 1029, 740,
[α]2D0 = +30 (c = 0.5, CH2Cl2). H NMR (300 MHz, CDCl3)
699. MS (m/z) = 306 (M ); Anal. calcd for C19H34N2O: C
1
+
δH 0.89 (d, J = 6.3 Hz, 12H), 1.08-1.46 (m, 4H), 1.46-1.66
(m, 2H), 2.39 (s, 3H), 2.51-2.70 (m, 3H), 3.23-3.33 (m, 3H),
74.46, H 11.18, N 9.14; found C 74.53, H 11.15, N 9.19.
(S)-2-(((S)-2-(Benzylamino)-4-methylpentyl)amino)-3-
methylbutan-1-ol (1l): Colorless oil (248 mg, 85%). [α]D20
13
3.54-3.59 (dd, 1H). C NMR (75.46 MHz, CDCl3) δC 21.7,
1
21.9, 23.7, 23.8, 24.6, 24.5, 30.6, 31.2, 33.1, 54.5, 61.9, 65.3,
= +90 (c = 0.8, CH2Cl2). H NMR (300 MHz, CDCl3) δH
−1
66.3. FT-IR (KBr, cm ) 3409, 2951, 2858, 2795, 1207,
0.88-0.99 (m, 12H), 1.24-1.28 (m, 1H), 1.40-1.50 (m, 1H),
1.63-1.65 (m, 1H), 1.75-1.91 (m, 1H), 2.33 (br s, 1H), 2.44-
2.56 (m, 1H), 2.67-2.70 (br d, 2H), 3.25-3.49 (m, 1H), 3.59-
+
1044. MS (m/z) = 230 (M ); Anal. calcd for C13H30N2O: C
67.77, H 13.12, N 12.16; found C 67.87, H 13.18, N 12.14.
(S)-2-(((S)-4-Methyl-2-(methylamino)pentyl)amino)-3-
phenylpropan-1-ol (1h): Light yellow oil (205 mg, 78%).
13
3.67 (m, 1H), 3.78 (br s, 2H), 7.33 (br s, 5H). C NMR
(75.46 MHz, CDCl3) δC 18.3, 18.4, 18.7, 18.9, 20.5, 35.4,
35.5, 37.6, 51.4, 50.4, 60.3, 62.0, 123.2, 133.5, 124.5, 124.6.
[α]2D0 = +85.71 (c = 0.1, CH2Cl2). H NMR (300 MHz, CDCl3)
1
−1
δH 0.88 (d, J = 6.5 Hz, 6H), 1.04-1.19 (m, 1H), 1.30-1.43 (m,
1H), 1.43-1.62 (m, 1H), 2.28 (t, 1H), 2.34 (s, 3H), 2.48 (t,
1H), 2.52-2.61 (m, 1H), 2.63-2.68 (dd, 1H), 2.70-2.73 (d, J =
6.9 Hz, 2H), 2.79-2.90 (m, 1H), 3.32-3.38 (dd, J = 10.8 Hz,
3J = 6.4 Hz, 1H), 3.57-3.62 (dd, J = 10.8 Hz, J = 3.6 Hz,
FT-IR (KBr, cm ) 3389, 3033, 2967, 2869, 1365, 1104, 1048,
+
740, 699. MS (m/z) = 292 (M ); Anal. calcd for C18H32N2O:
C 73.92, H 11.03, N 9.58; found C 73.99, H 11.08, N 9.55.
Synthesis of (S)-N2-((S)-1-Hydroxy-3-methylbutan-2-
yl)-N1-methyl-1-phenylethane-1,2-diaminium Chloride:
To a solution of diamine 1b (1 mmol) in dry diethyl ether (5
2
2
3
13
1H), 7.18-7.32 (m, 5H). C NMR (75.46 MHz, CDCl3) δC