appearance pale yellow liquid; FTIR (liquid film) nmax 3413, 2968,
1730, 1600, 1513, 1228, 732 cm-1; 1H NMR CDCl3 d (ppm) 0.92
(3H, CH3, t, J = 7.3 Hz), 1.00 (3H, CH3, t, J = 7.28 Hz), 1.43–1.56
(2H, CH2, m), 1.59–1.71 (2H, CH2, m), 3.06–3.11 (1H, CH, dt,
J = 5.3, 7.3 Hz), 3.45–3.49 (1H, CH, dq, J = 3.9, 5.3 Hz), 3.74
(3H, OCH3, s), 6.61–6.64 (2H, CH Ar, m, J = 8.9 Hz), 6.75–6.77
(2H, CH Ar, m, J = 8.9 Hz); 13C NMR (CDCl3) d (ppm) 10.1,
10.4, 24.8, 26.9, 55.8, 61.2, 74.3, 115.0, 115.7, 142.1, 152.6; MS
(m/z) 223 (6), 206 (12), 194 (2), 176 (6), 164 (100), 134 (15);
HRMS calcd for C13H21NO2: 223.1572; found 223.1581; mix A
and B (ratio 25/75); appearance pale yellow liquid; FTIR (liquid
film) nmax 3413, 2968, 1730, 1600, 1513, 1228, 732 cm-1; 1H NMR
CDCl3 d (ppm) 0.92 (3H, CH3 A, t, J = 7.3 Hz), 0.96 (3H, CH3 B,
t, J = 7.3 Hz), 1.00 (3H, CH3 A, t, J = 7.3 Hz), 1.01 (3H, CH3 B, t,
J = 7.3 Hz), 1.42–1.68 (8H, 2CH2 A + 2CH2 B, m), 3.08–3.12 (1H,
CH A, dt, J = 5.3, 7.3 Hz), 3.22 (1H, CH B, dt, J = 4.5, 8.4 Hz),
3.47–3.52 (1H, CH A, dt, J = 3.9, 5.3 Hz), 3.63–3.67 (1H, CH B,
dt, J = 3.6, 7.8 Hz), 3.74 (3H, OCH3 B, s), 3.76 (3H, OCH3 A, s),
6.66–6.69 (4H, CH Ar A + B, m), 6.76–6.78 (4H, CH Ar A+ B,
m); 13C NMR (CDCl3) d (ppm) 10.1, 10.4, 10.7, 11.1, 22.7, 24.8,
26.9, 25.7, 55.8 (2 C, A + B), 61.4, 61.6, 73.9, 74.3, 115.0 (2 C,
A + B), 115.8, 116.0, 141.4, 141.9, 152.8, 152.9; MS (m/z) 223 (6),
206 (12), 194 (2), 176 (6), 164 (100), 134 (15); HRMS calcd for
C13H21NO2: 223.1572; found 223.1569 (mix A + B).
13C NMR (CDCl3) d (ppm) 9.8, 11.5, 21.9, 26.7, 30.6, 66.9, 72.4,
114.2, 117.8, 129.1, 152.3; MS (m/z) 207 (3), 190 (2), 178 (3), 148
(100), 132 (13), 77 (13); HRMS calcd for C13H21NO: 207.1623;
found 207.1630; Diastereoisomer B (Rf minor = 0.34); appearance
pale yellow liquid; FTIR (liquid film) nmax 3627, 3425, 2969, 1598,
1505, 1216, 755; 1H NMR CDCl3 d (ppm) 0.84 (3H, CH3, t, J =
7.3 Hz), 0.94 (3H, CH3, t, J = 7.3 Hz), 1.28–1.37 (1H, CH, m),
1.54–1.72 (3H, CH2 + OH, m, D2O ex), 1.83–1.93 (1H, CH, m),
2.76 (3H, CH3, s), 3.56–3.64 (1H, CH2, m), 6.66 (1H, CH Ar, t,
J = 7.3 Hz), 6.77–6.79 (2H, CH Ar, m, J = 8.9 Hz), 7.18–7.23 (2H,
CH Ar, m, J = 7.3, 8.9 Hz); 13C NMR (CDCl3) d (ppm) 10.3, 11.3,
21.5, 27.7, 31.3, 64.0, 75.7, 112.4, 116.1, 129.1, 151.1; MS (m/z)
207 (3), 190 (2), 178 (3), 148 (100), 132 (13), 77 (13); HRMS calcd
for C13H21NO: 207.1623; found 207.1620.
3-(Benzyl(methyl)amino)hexan-3-ol,
3e. Crude
reaction
≥ 95%, no purification necessary to obtain mix of the two
diastereoisomers A and B in a 1/1 ratio; appearance colourless
liquid; 1H NMR (CDCl3) d (ppm) 1.00 (3H, CH3, t, J = 7.4 Hz),
1.01 (3H, CH3, t, J = 7.4 Hz), 1.03 (3H, CH3, t, J = 7.4 Hz), 1.06
(3H, CH3, t, J = 7.4 Hz), 1.26–1.75 (8H, 4 CH2, m), 2.21 (3H,
CH3, s), 2.24 (3H, CH3, s), 2.33–2.38 (1H, CH, m), 2.56–2.60
(1H, CH, m), 3.23–3.32 (1H, CH, m), 3.55–3.59 (1H, CH, m),
3.61 (1H, CH benz, d, J = 13.4 Hz), 3.64 (1H, CH benz, d, J =
13.4 Hz), 3.71 (1H, CH benz, d, J = 13.4 Hz), 3.78 (1H, CH benz,
d, J = 13.4 Hz), 7.22–7.31 (10H, CH Ar, m); 13C NMR (CDCl3)
d (ppm) 10.2, 11.2, 12.3, 13.7, 18.7, 19.1, 23.1, 26.5, 26.7, 26.9,
36.1, 38.7, 59.3, 59.9, 68.4, 69.8, 71.5, 73.0, 126.9, 127.1, 128.2,
128.4, 128.5, 128.8, 139.2, 140.0; ESI-MS m/z 222 [M + H], 244
[M + Na]; HRMS calcd for C14H23NO: 221.1780; found 221.1786
(mix A + B).
4-(p-Tolylamino)hexan-3-ol, 3b. The mix of the diastereoiso-
mers A and B (Rf 0.35) was isolated by FCC (Hexane/EtOAc,
6/4) in a ratio 3 : 2; appearance colourless liquid; total yield 76%,
1H NMR (CDCl3) d (ppm) 0.98–1.08 (12 H, 4 CH3, m) 1.44–1.62
(4H, 2CH2, m, A), 1.65–1.77 (4H, 2CH2, m, B), 2.29 (6H, 2CH3,
s), 3.21–3.25 (1H, CH, m, A), 3.31–3.35 (1H, CH, m, B), 3.53–3.57
(1H, CH, m, A), 3.65–3.69 (1H, CH, m, B), 6.62–6.64 (4H, 2CH
Ar A + 2CH Ar B, m), 7.01–7.03 (4H, 2CH Ar A + 2CH Ar B, m);
13C NMR (CDCl3) d (ppm) 10.3, 10.6, 10.7, 11.1, 20.3, 22.9, 25.2,
25.9, 27.0, 59.7, 59.8, 74.3, 74.5, 113.8, 126.6, 126.7, 129.9, 146.1,
146.5; ESI-MS m/z 208 [M + H], 230 [M + Na]; HRMS calcd for
C13H21NO: 207.1623; found 207.1615 (mix A + B).
4-(Piperidin-1-yl)hexan-3-ol, 3f . Diastereoisomers A and B
were isolated by FCC (CHCl3–MeOH, 8/2); total yield 43%.
Diastereoisomer A (Rf major = 0.38); appearance colourless liquid;
1H NMR (CDCl3) d (ppm) 0.99 (3H, CH3, t, J = 7.4 Hz), 1.04 (3H,
CH3, t, J = 7.4 Hz), 1.24–1.34 (4H, m, 2 CH2), 1.45–1.49 (2H, m,
CH2), 1.54–1.67 (4H, m, 2CH2), 2.11–2.16 (1H, m, CH), 2.45–2.50
4-(4-Bromophenylamino)hexan-3-ol, 3c. The mix of di-
astereoisomers A and B (Rf 0.35) in a 1 : 1 ratio was isolated
by FCC (Hexane/EtOAc 6 : 4); total yield 52%; appearance pale
(2H, m, CH2), 2.72–2.78 (2H, m, CH2), 3.15–3.20 (1H, m, CH); 13
C
NMR (CDCl3) d (ppm) 10.2, 13.7, 19.3, 24.6, 26.7, 27.1, 51.2, 70.6,
71.3. ESI-MS m/z 186 [M + H], 208 [M + Na]; Diastereoisomer B
(Rf minor = 0.32); appearance colourless liquid;1H NMR (CDCl3)
d (ppm) 0.96 (3H, CH3, t, J = 7.3 Hz), 1.00 (3H, CH3, t, J =
7.3 Hz), 1.26–1.31 (1H, m, CH), 1.41–1.49 (4H, m, 2CH2), 1.55–
1.70 (5H, m, 2CH2 + 1CH), 2.40–2.45 (1H, m, CH), 2.53–2.59
(2H, m, CH2), 2.65–2.71 (2H, m, CH2), 3.48–3.52 (1H, m, CH);
13C NMR (CDCl3) d (ppm) 11.5, 12.4, 18.6, 24.6, 26.1, 26.7, 52.3,
70.2, 72.4. ESI-MS m/z 186 [M + H], 208 [M + Na]; HRMS calcd
for C11H23NO: 185.1780; found 185.1773 (mix A + B).
1
yellow liquid; H NMR (DMSO) d (ppm) 0.78 (3H, CH3, t, J =
7.5 Hz), 0.82 (3H, CH3, t, J = 7.3 Hz), 0.83 (3H, CH3, t, J =
7.5 Hz), 0.85 (3H, CH3, t, J = 7.4 Hz), 1.21–1.78 (12H, 4 CH2,
m) 3.03–3.08 (1H, CH, m), 3.17–3.40 (3H, CH, m) 6.51–6.53 (4H,
CH Ar, d, J = 8.8 Hz) 7.10– 7.12 (4H, CH Ar, d, J = 8.9 Hz);
13C NMR (CDCl3) d (ppm) 10.1, 10.5, 10.5, 10.9 22.7, 25.1, 26.0,
26.9, 58.8, 59.2, 74.3, 74.4, 109.9, 116.6, 131.8, 145.4; MS (m/z)
271 (8) 212 (100); HMRS calcd for C12H18BrNO: 271.0572, found
271.0569 (mix A+B).
5-(4-Methoxy-phenylamino)-octan-4-ol, 4a16. Diastereoiso-
mer A (Rf major = 0.37) and a mix of diastereoisomers A
and B (Rf minor = 0.35) in a ratio 3/7 were isolated by FCC
(Hexane/EtOAc, 7/3); total yield 24%. Diastereoisomer A;
appearance pale orange liquid; FTIR (liquid film) nmax 3418,
3018, 2960, 1512, 1216 cm-1; 1H NMR CDCl3 d (ppm) 0.88 (3H,
CH3, t, J = 7.1 Hz), 0.94 (3H, CH3, t, J = 7.1 Hz), 1.25–1.63 (8H,
4CH2, m), 3.11–3.15 (1H, CH, m), 3.50–3.54 (1H, CH, m), 3.74
(3H, OCH3, s), 6.61 (2H, 2ArH, d, J = 9.0 Hz), 6.75 (2H, 2ArH,
d, J = 9.0 Hz); 13C NMR (CDCl3) d (ppm) 14.4, 14.5, 19.4, 19.7,
4-(Methyl-phenyl-amino)-hexan-3-ol, 3d16. Diastereoisomers
A and B were isolated by FCC (Hexane/EtOAc, 8/2); total yield
44%. Diastereoisomer A (Rf major = 0.37); appearance pale yellow
liquid; FTIR (liquid film) nmax 3627, 3425, 2969, 1598, 1505, 1216,
755; 1H NMR CDCl3 d (ppm) 0.75 (3H, CH3, t, J = 7.6 Hz), 1.07
(3H, CH3, t, J = 7.6 Hz), 1.42–1.49 (1H, CH, m), 1.52–1.59 (2H,
CH2, m), 1.66–1.75 (1H, CH, m), 2.78 (3H, CH3, s), 3.51–3.58
(2H, CH2, m), 6.75 (1H, CHAr, t, J = 7.3 Hz), 6.89–6.91 (2H, CH
Ar, m, J = 8.9 Hz), 7.20–7.24 (2H, CH Ar, m, J = 7.3, 8.9 Hz);
This journal is
The Royal Society of Chemistry 2011
Org. Biomol. Chem., 2011, 9, 3759–3767 | 3765
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