The Journal of Organic Chemistry
NOTE
N-[(1S)-1-((1S)-1-[[(Phenylmethyl)oxy]methyl]propyl)-2-
propen-1-yl]aniline, 9a: yellow oil; δH 7.38ꢀ7.25 (5H, m),
7.13ꢀ7.07 (2H, m), 6.60 (1H, tt, J = 7.3, 1.3), 6.50 (2H, d, J = 7.6), 5.74
(1H, ddd, J = 16.1, 10.6, 5.5), 5.20 (1H, dt, J = 17.1, 1.5), 5.13 (1H, dt,
J = 11.5, 1.5), 4.74 (1H, br s), 4.50 (1H, d, J = 11.6), 4.47 (1H, d, J = 11.6),
4.00 (1H, br s), 3.69 (1H, dd, J = 9.3, 2.8), 3.50 (1H, dd, J = 9.3, 4.8),
1.72ꢀ1.46 (3H, m), 0.92 (3H, t, J = 7.6); δC 148.1, 138.7, 138.3, 129.0,
128.4, 127.6, 127.5, 116.3, 115.7, 112.7, 73.4, 70.3, 57.7, 44.7, 21.7, 12.0;
νmax/cmꢀ1 3403, 2962, 2873, 1600, 1505, 1317, 1091, 1061, 992; HRMS
(ESþ) [M þ H]þ 296.2005, C20H26ON requires 296.2014.
(1H, ddd, J = 16.9, 10.6, 5.8), 5.23ꢀ5.11 (2H, m), 4.52 (2H, s), 3.97
(1H, br s), 3.85 (1H, t, J = 5.3), 3.63ꢀ3.56 (1H, m), 3.55ꢀ3.44 (1H, m),
1.86ꢀ1.74 (1H, m), 1.70ꢀ1.43 (3H, m), 1.41ꢀ1.27 (1H, m), 0.91 (3H, t,
J = 7.4); δC 148.0, 138.5, 138.4, 129.1, 128.4, 127.7, 127.6, 116.8, 115.9,
113.1, 73.1, 69.0, 57.9, 41.6, 29.9, 23.5, 11.7; νmax/cmꢀ1 3364, 3027, 2960,
2929, 2869, 1600, 1501, 1454, 1431, 1315, 1094, 1028, 992; HRMS
(ESþ) [M þ H]þ 310.2164, C21H28ON requires 310.2171.
(3S,4R)-4-Ethyl-N-(phenylmethyl)-6-[(phenylmethyl)oxy]-
1-hexen-3-amine, 9h: yellow oil; δH 7.36ꢀ7.17 (10H, m), 5.63 (1H,
ddd, J = 17.1, 10.6, 8.6), 5.16 (1H, dd, J = 10.6, 2.0), 5.07 (1H, dd, J = 17.1,
2.0), 4.46 (2H, s), 3.81 (1H, d, J = 13.6), 3.57 (1H, d, J = 13.1), 3.51ꢀ3.45
(2H, m), 2.98 (1H, dd, J = 8.3, 5.3), 1.79ꢀ1.68 (1H, m), 1.67ꢀ1.39
(3H, m), 1.28ꢀ1.11 (2H, m), 0.84 (3H, t, J = 7.3); δC 141.0, 139.3,
138.7, 128.3, 128.2, 128.1, 127.5, 127.4, 126.7, 116.4, 72.8, 69.0, 63.2,
51.4, 41.6, 30.0, 22.8, 11.7; νmax/cmꢀ1 3064, 3028, 2959, 2929, 2870,
1724, 1495, 1453, 1362, 1246, 1097, 1027, 997;HRMS (ESþ) [M þ H]þ
324.2313, C22H30ON requires 324.2327.
(3S,4S)-N-(Phenylmethyl)-4-[[(phenylmethyl)oxy]methyl]-
1-hexen-3-amine, 9b: yellow oil; δH 7.36ꢀ7.17 (10H, m), 5.65 (1H,
ddd, J = 17.5, 9.3, 8.9), 5.17 (1H, dd, J = 9.6, 2.0), 5.08 (1H, ddd, J = 17.5,
2.0, 1.0), 4.49 (1H, d, J = 11.9), 4.45 (1H, d, J = 11.9), 3.82 (1H, d, J =
13.1), 3.60 (1H, d, J = 13.1), 3.55 (1H, dd, J = 9.1, 4.5), 3.46 (1H, dd, J =
9.1, 6.5), 3.17 (1H, dd, J = 8.6, 6.0), 1.70ꢀ1.48 (3H, m), 1.34ꢀ1.14 (1H,
m) 0.87 (3H, t, J = 7.6); δC 141.0, 139.5, 138.6, 128.3, 128.2, 128.1,
127.5, 127.4, 126.6, 116.6, 73.1, 70.9, 62.1, 51.4, 44.9, 20.8, 12.0; νmax
/
(3S,4R)-4-Ethyl-N-(2-furanylmethyl)-6-[(phenylmethyl)oxy]-
1-hexen-3-amine, 9i: yellow oil; δH 7.39ꢀ7.23 (6H, m), 6.28 (1H,
dd, J = 3.0, 2.0), 6.11 (1H, d, J = 2.5), 5.62 (1H, ddd, J = 17.1, 10.3, 8.3),
5.17 (1H, dd, J = 10.6, 1.8), 5.09 (1H, ddd, J = 17.1, 2.0, 1.0), 4.47 (2H, s),
3.79 (1H, d, J= 14.6), 3.61 (1H, d, J = 14.6), 3.48 (2H, td, J= 6.8, 1.0), 2.99
(1H, dd, J = 8.6, 5.0), 1.75ꢀ1.42 (5H, m), 1.26ꢀ1.11 (1H, m), 0.84
(3H, t, J = 7.3); δC 154.3, 141.5, 138.7, 138.6, 128.2, 127.5, 127.4, 116.9,
110.0, 106.6, 72.8, 68.8, 62.8, 43.8, 41.5, 29.9, 22.7, 11.7; νmax/cmꢀ1 3067,
3030, 2959, 2930, 2870, 1725, 1498, 1454, 1361, 1203, 1147, 1096, 1027,
1005; HRMS (ESþ) [M þ H]þ 314.2108, C20H28O2N requires
314.2120.
N-[(1S)-1-((1R)-1-[[(Phenylmethyl)oxy]methyl]propyl)-2-
propen-1-yl]aniline, ent-10a: yellow oil; δH 7.32ꢀ7.19 (5H, m),
7.05 (2H, t, J = 7.8), 6.56 (1H, t, J = 7.3), 6.45 (2H, d, J = 8.1), 5.67 (1H,
ddd, J = 16.9, 10.3, 6.0), 5.18ꢀ5.06 (2H, m), 4.67 (1H, br s), 4.45 (1H, d,
J = 12.1), 4.39 (1H, d, J = 12.1), 4.00 (1H, br s), 3.48ꢀ3.41 (2H, m),
1.94ꢀ1.76 (1H, m), 1.39ꢀ1.14 (2H, m), 0.91 (3H, t, J = 7.6); δC 147.8,
138.2, 136.7, 129.0, 128.4, 127.7, 127.6, 116.7, 116.6, 113.1, 73.4, 71.4,
57.6, 44.6, 21.1, 12.4; νmax/cmꢀ1 3403, 2962, 2873, 1600, 1505, 1317,
1091, 1061, 992; HRMS (ESþ) [M þ H]þ 296.2008, C20H26ON
requires 296.2014.
(3S,4R)-N-(Phenylmethyl)-4-[[(phenylmethyl)oxy]methyl]-
1-hexen-3-amine, ent-10b: yellow oil; δH 7.34ꢀ7.17 (10H, m),
5.68 (1H, ddd, J = 17.1, 10.3, 8.3), 5.17 (1H, dd, J = 10.6, 2.0), 5.10 (1H,
ddd, J = 17.1, 2.0, 1.0), 4.46 (1H, d, J = 11.6), 4.43 (1H, d, J = 11.6), 3.82
(1H, d, J = 13.1), 3.58 (1H, d, J = 13.6), 3.54 (1H, dd, J = 9.1, 6.5), 3.41
(1H, dd, J = 9.1, 5.0), 3.16 (1H, dd, J = 8.6, 4.5), 1.79ꢀ1.69 (1H, m), 1.65
(1H, s), 1.48ꢀ1.33 (2H, m), 0.89 (3H, t, J = 7.3); δC 140.9, 139.0, 138.6,
128.3, 128.2, 128.1, 127.5, 127.4, 126.6, 116.6, 73.1, 71.0, 62.5, 51.3, 44.8,
20.8, 12.0; νmax/cmꢀ1 3064, 3028, 2961, 2872, 1725, 1494, 1453, 1363,
1095, 1027, 996; HRMS (ESþ) [M þ H]þ 310.2162, C21H28ON
requires 310.2171.
(3S,4R)-N-(2-Furanylmethyl)-4-[[(phenylmethyl)oxy]methyl]-
1-hexen-3-amine, ent-10c: yellow oil; δH 7.37ꢀ7.25 (6H, m), 6.29
(1H, dd, J = 3.0, 2.0), 6.12 (1H, d, J = 3.0), 5.66 (1H, ddd, J = 17.1, 10.1, 8.6),
5.18 (1H, dd, J = 10.1, 2.0), 5.08 (1H, ddd, J = 17.1, 2.0, 1.0), 4.46 (2H, s),
3.81 (1H, d, J = 14.6), 3.61 (1H, d, J = 14.1), 3.53 (1H, dd,
J = 9.6, 6.5), 3.40 (1H, dd, J = 9.3, 5.3), 3.15 (1H, dd, J = 8.3, 4.3),
1.82 (1H, br s), 1.78ꢀ1.69 (1H, m), 1.43ꢀ1.34 (2H, m), 0.88 (3H, t,
J = 7.1); δC 154.3, 141.5, 138.6, 138.5, 128.3, 127.5, 127.4, 117.0, 110.0,
106.6, 73.2, 70.9, 62.3, 44.7, 43.9, 20.8, 11.8; νmax/cmꢀ1 3067, 3030,
2962, 2873, 1725, 1498, 1454, 1361, 1147, 1094, 1075, 1004; HRMS
(ESþ) [M þ H]þ 300.1952, C19H26O2N requires 300.1964.
N-[(1S)-1-[(1S)-1-Ethyl-4-phenylbutyl]-2-propen-1-yl]ani-
line, ent-10d: yellow oil; δH 7.30ꢀ7.24 (2H, m), 7.21ꢀ7.10 (5H, m),
6.66 (1H, t, J = 7.3), 6.57 (2H, d, J = 7.6), 5.71 (1H, ddd, J = 17.0, 10.7,
6.0), 5.20ꢀ5.11 (2H, m), 3.90 (1H, t, J = 5.0), 3.63 (1H, br s), 2.59 (2H,
cmꢀ1 3064, 3028, 2961, 2872, 1725, 1494, 1453, 1363, 1095, 1027, 996;
HRMS (ESþ) [M þ H]þ 310.2158, C21H28ON requires 310.2171.
(3S,4S)-N-(2-Furanylmethyl)-4-[[(phenylmethyl)oxy]methyl]-
1-hexen-3-amine, 9c: yellow oil; δH 7.35ꢀ7.24 (6H, m), 6.28 (1H,
dd, J = 3.3, 2.8), 6.11 (1H, dd, J = 3.0, 1.0), 5.62 (1H, ddd, J = 17.1, 10.1,
8.6), 5.16 (1H, dd, J = 10.1, 2.0), 5.09 (1H, ddd, J = 17.1, 2.0, 1.0), 4.49
(1H, d, J = 12.1), 4.44 (1H, d, J = 12.1), 3.79 (1H, d, J = 14.6), 3.61 (1H,
d, J = 14.6), 3.52 (1H, dd, J = 9.6, 4.5), 3.42 (1H, dd, J = 8.6, 5.5), 3.15
(1H, dd, J = 8.6, 5.5), 1.74 (1H, br s), 1.68ꢀ1.59 (1H, m), 1.57ꢀ1.47
(1H, m), 1.28ꢀ1.16 (1H, m), 0.86 (3H, t, J = 7.6); δC 154.4, 141.5,
139.0, 138.6, 128.2, 127.5, 127.4, 117.1, 110.0, 106.6, 73.0, 70.9, 62.4,
44.7, 43.8, 20.8, 11.9; νmax/cmꢀ1 3067, 3030, 2962, 2873, 1725, 1498,
1454, 1361, 1147, 1094, 1075, 1004; HRMS (ESþ) [M þ H]þ
300.1953, C19H26O2N requires 300.1964.
N-[(1S)-1-[(1R)-1-Ethyl-4-phenylbutyl]-2-propen-1-yl]ani-
line, 9d: yellow oil; δH 7.30ꢀ7.23 (2H, m), 7.20ꢀ7.09 (5H, m), 6.65
(1H, t, J = 7.6), 6.56 (2H, d, J = 7.6), 5.71 (1H, ddd, J = 17.0, 10.7, 6.0),
5.19ꢀ5.10 (2H, m), 3.89 (1H, br s), 3.61 (1H, br s), 2.60 (2H, t, J = 7.6),
1.79ꢀ1.58 (2H, m), 1.55ꢀ1.41 (3H, m), 1.40ꢀ1.26 (2H, m), 0.89 (3H,
t, J = 7.1); δC 147.8, 142.4, 138.3, 129.1, 128.4, 128.3, 125.7, 117.0,
115.7, 113.2, 57.6, 44.3, 36.2, 29.4, 29.2, 23.0, 11.9; νmax/cmꢀ1 3420,
3054, 3024, 2930, 2860, 1600, 1501, 1454, 1429, 1313, 1253, 992;
HRMS (ESþ) [M þ H]þ 294.2221, C21H28N requires 294.2222.
(3S,4R)-4-Ethyl-7-phenyl-N-(phenylmethyl)-1-hepten-3-
amine, 9e: yellow oil; δH 7.35ꢀ7.13 (10H, m), 5.62 (1H, ddd, J = 17.1,
10.6, 8.6), 5.15 (1H, dd, J = 10.6, 2.0), 5.05 (1H, ddd, J = 17.1, 2.0, 1.0),
3.82 (1H, d, J = 13.1), 3.59 (1H, d, J = 13.1), 2.98 (1H, dd, J = 8.1, 5.0),
2.58 (1H, d, J = 7.5), 2.56 (1H, d, J = 7.5), 1.66ꢀ1.11 (8H, m), 0.82 (3H, t,
J = 7.6); δC 142.7, 141.0, 139.4, 128.3 ( ꢁ 2), 128.2 ( ꢁ 2), 126.7, 125.6,
116.3, 63.0, 51.4, 44.3, 36.3, 29.3, 29.0, 22.5, 11.8; νmax/cmꢀ1 3063, 3026,
2929, 2857, 1723, 1494, 1453, 1224, 1101, 1053, 996; HRMS (ESþ)
[M þ H]þ 308.2369, C22H30N requires 308.2378.
(3S,4R)-4-Ethyl-N-(2-furanylmethyl)-7-phenyl-1-hepten-
3-amine, 9f: yellow oil; δH 7.32 (1H, d, J = 2.5), 7.28ꢀ7.22 (2H, m),
7.18ꢀ7.12 (3H, m), 6.30ꢀ6.26 (1H, m), 6.11 (1H, d, J = 4.0), 5.59
(1H, ddd, J = 17.1, 10.1, 8.1), 5.14 (1H, dd, J = 9.6, 2.0), 5.04 (1H, ddd,
J = 17.1, 2.0, 1.0), 3.79 (1H, d, J = 14.6), 3.60 (1H, d, J = 14.6), 2.98 (1H,
dd, J = 8.1, 4.5), 2.58 (1H, d, J = 7.5), 2.54 (1H, d, J = 7.6), 1.61ꢀ1.28
(7H, m), 1.21ꢀ1.08 (1H, m) 0.82 (3H, t, J = 7.6); δC 154.3, 142.6,
141.5, 138.9, 128.3, 128.2, 125.6, 116.8, 110.0, 106.7, 62.5, 44.2, 43.8,
36.2, 29.3, 28.9, 22.4, 11.8; νmax/cmꢀ1 3064, 3026, 2930, 2861, 1723,
1602, 1496, 1455, 1147, 1097, 1076, 1006; HRMS (ESþ) [M þ H]þ
298.2159, C20H28NO requires 298.2171.
N-((1S)-1-[(1R)-1-Ethyl-3-[(phenylmethyl)oxy]propyl]-2-
propen-1-yl)aniline, 9g: yellow oil; δH 7.38ꢀ7.24(5H, m), 7.11ꢀ7.05
(2H, m), 6.62 (1H, tt, J = 7.3, 1.3), 6.51 (2H, dd, J = 8.8, 1.3), 5.73
5499
dx.doi.org/10.1021/jo200720c |J. Org. Chem. 2011, 76, 5495–5501