U. Azzena et al. / Tetrahedron 56 (2000) 3775±3780
3779
C14H23NO requires C, 75.95; H, 10.49]; Rf (10% Et3N/petro-
leum ether) 0.61 and 0.45; bp 1108C/1 mmHg; 1st dia-
stereoisomer solidi®es upon standing, white solid: mp 71±
748C (petroleum ether); nmax 3453, 2950, 1460, 1360,
1010 cm21; 1st diastereoisomer: dH 0.73 (9H, s, 3£CH3),
1.60 (1H, b s, OH), 2.13 (6H, s, 2£CH3N), 3.43 (1H, d,
J10.2 Hz, CHPh), 3.73 (1H, d, J10.2 Hz, CHO), 7.11±
7.18 (2H, m, ArH), 7.28±7.38 (3H, m, ArH); dC 26.9, 34.7,
40.7, 69.8, 74.3, 127.5, 127.7, 130.0, 134.6; 2nd diastereo-
isomer: dH 0.73 (9H, s, 3£CH3), 2.20 (6H, s, 2£CH3N), 3.14
(1H, d, J4.0 Hz, CHPh), 3.84 (1H, d, J4.0 Hz, CHO),
7.25±7.36 (5H, m, ArH); dC 26.5, 29.8, 34.3, 43.8, 72.8,
127.5, 127.9, 130.2, 138.0.
2-N-Methyl-N-(10-phenyl)pentylaminoethanol
(3dd).
Puri®ed by ¯ash chromatography (petroleum ether/AcOEt/
Et3N3:7:1), colourless oil; [Found: C, 75.63; H, 10.69.
C14H23NO requires C, 75.95; H, 10.49]; Rf (petroleum
ether/AcOEt/Et3N3:7:1) 0.41; bp 1128C/760 mmHg;
nmax 3390, 2950, 1500, 1480, 1040 cm21; dH 0.86 (3H, t,
J6.6 Hz, CH3), 1.07±1.38 (4H, m, (CH2)2), 1.71±1.95
(2H, m, CH2), 2.16 (3H, s, CH3N), 2.40±2.48 (1H, m,
CHN), 2.52±2.62 (1H, m, CHN), 3.48±3.63 (3H, m,
CH2O, CHAr), 7.18±7.36 (5H, m, ArH); dC 13.9, 22.7,
29.0, 31.7, 36.9, 54.9, 57.9, 68.6, 127.1, 128.0, 128.6, 139.3.
1-N-Methyl-N-(20-hydroxyethyl)amino-1-phenyl-2-methyl-
propan-2-ol (3de). Puri®ed by ¯ash chromatography (10%
Et3N/AcOEt), colourless oil; [Found: C, 69.78; H, 9.79.
C13H21NO2 requires C, 69.90; H, 9.50]; Rf (10% Et3N/
AcOEt) 0.42; bp 1268C/1 mmHg; nmax 3430, 2930, 1640,
1600, 1030 cm21; dH 1.18 (3H, s, CH3), 1.41 (3H, s, CH3),
2.26±2.37 (1H, m, CHN), 2.40 (2H, s, CH3N), 2.91 (1H,
ddd, J13.0, 8.0, 4.5 Hz, HCN), 3.42 (1H, s, CHAr), 3.56±
3.73 (2H, m, CH2O), 7.29±7.44 (5H, m, ArH); dC 28.3,
29.4, 40.4, 57.1, 59.1, 74.2, 76.3, 127.3, 127.9, 130.7, 135.8.
N,N-Dimethyl-1-(20-methoxy)phenylpentylamine (3bc).
Puri®ed by ¯ash chromatography (petroleum ether/AcOEt/
Et3N8:2:1), colourless oil; [Found: C, 75.81; H, 10.58.
C14H23NO requires C, 75.95; H, 10.49]; Rf (petroleum
ether/AcOEt/Et3N8:2:1) 0.34; bp 858C/1 mmHg; nmax
3020, 2970, 1600, 1470, 1240; dH 0.82 (3H, t, J7.2 Hz,
CH3), 0.98±1.36 (4H, m, 2£CH2), 1.65±1.89 (2H, m, CH2),
2.17 (6H, s, 2£CH3N), 3.81 (3H, s, CH3O), 3.89 (1H, dd,
J9.6, 5.1 Hz, CH), 6.89 (1H, d, J8.4 Hz, ArH), 6.95 (1H,
td, J7.5, 0.9 Hz, ArH), 7.17±7.28 (2H, m, ArH); dC 14.0,
22.9, 28.3, 32.0, 42.5, 55.4, 60.9, 110.5, 120.1, 127.5, 128.5,
128.8, 158.0.
1-N-Methyl-N-(20-hydroxyethyl)amino-1-phenyl-3,3-di-
methylbutan-2-ol (3df). Puri®ed by ¯ash chromatography
(10% Et3N/AcOEt), colourless oil; [Found: C, 71.43; H,
10.35. C15H25NO2 requires C, 71.66; H, 10.04]; Rf (10%
Et3N/AcOEt) 0.40 and 0.39; bp 1408C/1 mmHg; nmax
3360, 2950, 1475, 1450, 1360 cm21; 1st diastereoisomer:
dH 0.75 (9H, s, 3£CH3), 2.18 (3H, s, CH3N), 2.30±2.45
(1H, m, CHN), 2.55±2.66 (1H, m, CHN), 3.59 (1H, d,
J9.6 Hz, CHAr), 3.69±3.75 (2H, m, CH2O), 3.80 (1H, d,
J9.6 Hz, CHO), 7.15±7.22 (2H, m, ArH), 7.28±7.38 (3H,
m, ArH); 2nd diastereoisomer: not obtained in a suf®ciently
pure form to unambiguously assign its 1H NMR resonances;
1st diastereoisomer: dC 26.9, 34.8, 37.5, 55.4, 59.6, 69.3,
74.4, 127.6, 127.9, 129.8, 135.2; 2nd diastereoisomer: dC
26.6, 35.1, 38.4, 56.1, 58.7, 70.8, 78.2, 127.2, 128.0,
130.6, 136.3.
N,N-Dimethyl-1-(20-methoxy)phenyl-2-methylpropyl-
amine (3bd). Puri®ed by ¯ash chromatography (petroleum
ether/AcOEt/Et3N8:2:1), colourless oil; [Found: C, 75.18;
H, 10.39. C13H21NO requires C, 75.30; H, 10.23]; Rf (petro-
leum ether/AcOEt/Et3N8:2:1) 0.58; bp 708C/1 mmHg;
nmax 3020, 2980, 1600, 1470, 1250; dH 0.71 (3H, d,
J6.6 Hz, CH3), 1.00 (3H, d, J6.6 Hz, CH3), 2.10 (6H,
s, 2£CH3N), 2.15±2.23 (1H, m, CH), 3.73 (1H, d,
J9.3 Hz, CHAr), 3.79 (3H, s, CH3O), 6.90 (1H, dd,
J8.4, 1.2 Hz, ArH), 6.95 (1H, dd, J7.5, 1.2 Hz, ArH),
7.14±7.25 (2H, m, ArH); dC 19.1, 20.5, 28.7, 41.7, 55.4,
65.9, 110.5, 119.7, 126.1, 127.3, 129.1, 158.5.
1-Phenyl-1-(N-piperidino)-2-methylpropan-2-ol (3cd).
Puri®ed by ¯ash chromatography (petroleum ether/AcOEt/
Et3N5:5:1), colourless oil; [Found: C, 76.93; H, 10.03.
C15H23NO requires C, 77.19; H, 9.95]; Rf (petroleum
ether/AcOEt/Et3N5:5:1) 0.45; bp 1458C/1 mmHg; nmax
3550, 3010, 2960, 1520, 1480, 1260 cm21; dH 1.16 (3H, s,
CH3) 1.24±1.36 (2H, m, CH2), 1.32 (3H, s, CH3), 1.50±1.66
(4H, m, 2£CH2), 2.18±2.34 (2H, b s, CH2), 2.66±2.78 (2H, b
s, CH2), 3.34 (1H, s, CH), 7.28±7.34 (5H, m, ArH); dC 24.2,
26.6, 26.9, 29.2, 53.9, 72.6, 79.8, 127.2, 127.7, 130.8, 135.8.
2-N-[10-(20,30-Dimethoxy)phenyl]ethyl-N-methylamino-
ethanol (3ec). Puri®ed by ¯ash chromatography (petroleum
ether/AcOEt/Et3N0.5:9.5:1), colourless oil; [Found: C,
65.17; H, 9.01. C13H21NO3 requires C, 65.23; H, 8.86]; Rf
(petroleum ether/AcOEt/Et3N0.5:9.5:1) 0.34; bp 1258C/
1 mmHg; nmax 3320, 2970, 1580, 1450, 1210 cm21; dH
1.34 (3H, d, J6.9 Hz, CH3), 2.18 (3H, s, CH3N), 2.53±
2.64 (2H, m, CH2N), 3.49±3.61 (2H, m, CH2O), 3.83 (3H,
s, CH3O), 3.87 (3H, s, CH3O), 4.18 (1H, q, J6.9 Hz, CH),
6.83 (1H, dd, J7.8, 1.5 Hz, ArH), 6.93 (1H, dd, J7.8,
1.5 Hz, ArH), 7.05 (1H, t, J7.8 Hz, ArH); dC 17.3, 37.1,
55.2, 55.4, 55.6, 58.3, 60.7, 110.8, 119.5, 123.7, 136.7,
147.0, 152.7.
2-N-Methyl-N-(10-phenyl)propylaminoethanol
(3dc).
Puri®ed by ¯ash chromatography (petroleum ether/AcOEt/
Et3N5:5:1), colourless oil; [Found: C, 74.29; H, 10.09.
C12H19NO requires C, 74.55; H, 9.93]; Rf (petroleum
ether/AcOEt/Et3N5:5:1) 0.50; bp 1308C/1 mmHg; nmax
3480, 2970, 1510, 1470, 1050 cm21; dH 0.84 (3H, t,
J7.5 Hz, CH3), 1.72±1.88 (1H, m, CH), 1.88±2.04 (1H,
m, CH), 2.17 (3H, s, CH3N), 2.40±2.50 (1H, m, CHN),
2.51±2.62 (1H, m, CHN), 3.42 (1H, dd, J8.7, 6.3 Hz,
CHAr), 3.47±3.64 (2H, m, CH2O), 7.17±7.37 (5H, m,
ArH); dC 11.6, 25.2, 37.2, 55.3, 58.3, 70.6, 127.4, 128.3,
128.9, 139.6.
1-N-(20-Hydroxy)ethyl-N-methyl-1-(20,30-dimethoxy)-
phenyl-2-methylpropan-2-ol (3ed). Puri®ed by ¯ash
chromatography (10% Et3N/AcOEt), white solid; [Found:
C, 63.31; H, 9.12. C15H25NO4 requires C, 63.57; H, 8.91]; Rf
(10% Et3N/AcOEt) 0.51; mp 91±938C (Et2O/pentane); nmax
(KBr) 3410, 2990, 1610, 1460, 1270 cm21; dH 1.17 (3H, s,
CH3), 1.44 (3H, s, CH3), 2.37 (3H, s, CH3N), 2.38±2.48 (1H,
m, CHN), 2.64 (2H, b s, OH), 2.76±2.85 (1H, m, CHN),
3.55±3.62 (1H, m, CHO), 3.64±3.72 (1H, m, CHO), 3.82