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F. Boukattaya et al.
Paper
Synthesis
Yield: 887 mg (73%); white solid; mp 150–151 °C; Rf = 0.23 (cyclohex-
ane–EtOAc, 80:20).
1H NMR (CDCl3, 400 MHz): δ = 8.22–8.20 (m, 1 H, ArH), 7.90 (d, J =
8.2 Hz, 1 H, ArH), 7.87–7.85 (m, 1 H, ArH), 7.57–7.40 (m, 4 H, ArH),
7.28–7.24 (m, 4 H, ArH), 7.19–7.13 (m, 6 H, ArH), 5.87 (br s, 1 H, NH),
4.89 (br s, 1 H, OH), 3.81 (s, 2 H, CH2OH), 2.62 (t, J = 7.4 Hz, 4 H,
CH2Ph), 1.82–1.55 (m, 8 H, CH2).
13C NMR (CDCl3, 100 MHz): δ = 170.9 (C=O), 141.9 (2 CAr), 134.7 (CAr),
133.8 (CAr), 130.8 (CAr), 130.0 (CAr), 128.5 (5 CAr), 128.4 (CAr), 127.4
(CAr), 126.6 (4 CAr), 126.1 (CAr), 125.2 (2 CAr), 124.7 (2 CAr), 67.7
(CH2OH), 62.2 (C), 36.2 (2 CH2), 34.1 (2 CH2), 25.3 (2 CH2).
IR (neat): 3237, 3051, 2970, 2855, 1626, 1562, 1460, 1350, 1261,
1175, 1061, 782, 737 cm–1
.
1H NMR (CDCl3, 400 MHz): δ = 8.24 (d, J = 8.2 Hz, 1 H, ArH), 7.90 (d, J =
8.5 Hz, 1 H, ArH), 7.87 (d, J = 7.8 Hz, 1 H, ArH), 7.59–7.49 (m, 3 H,
ArH), 7.44 (dd, J = 8.2, 7.0 Hz, 1 H, ArH), 6.10 (br s, 1 H, NH), 4.80 (br s,
1 H, OH), 3.75 (s, 2 H, CH2), 1.44 (s, 6 H, CH3).
13C NMR (CDCl3, 50 MHz): δ = 170.8 (C=O), 134.7 (CAr), 133.7 (CAr),
130.7 (CAr), 130.0 (CAr), 128.4 (CAr), 127.3 (CAr), 126.6 (CAr), 125.1 (CAr),
124.8 (CAr), 124.7 (CAr), 70.8 (CH2), 57.1 (C), 24.9 (2 CH3).
HRMS (ESI+): m/z [M + Na+] calcd for C31H33NNaO2: 474.2404; found:
474.2399.
HRMS (ESI+): m/z [M + Na+] calcd for C15H17NNaO2: 266.1151; found:
266.1162.
N-(2-Hydroxy-1,1-diphenylethyl)-1-naphthamide (2if)
Purification by flash chromatography afforded 2if.
Yield: 1.29 g (70%); pale-yellow foam; mp 186 °C; Rf = 0.17 (petro-
leum ether–EtOAc, 80:20).
N-[6-(Hydroxymethyl)undecan-6-yl]-1-naphthamide (2ic)
Purification by flash chromatography afforded 2ic.
IR (neat): 3222, 3052, 1639, 1510, 1493, 1257, 758, 782, 698 cm–1
.
Yield: 1.21 g (68%); white solid; mp 73–74 °C; Rf = 0.37 (CH2Cl2).
1H NMR (CDCl3, 400 MHz): δ = 8.34 (d, J = 7.9 Hz, 1 H, ArH), 7.95 (d, J =
8.2 Hz, 1 H, ArH), 7.89 (dd, J = 7.5, 2.0 Hz, 1 H, ArH), 7.74 (d, J = 7.0 Hz,
1 H, ArH), 7.59–7.56 (m, 2 H, ArH), 7.48 (dd, J = 8.4, 7.0 Hz, 1 H, ArH),
7.42–7.32 (m, 10 H, ArH), 6.90 (br s, 1 H, NH), 5.29 (br s, 1 H, OH),
4.60 (s, 2 H, CH2).
13C NMR (CDCl3, 100 MHz): δ = 170.8 (C=O), 142.0 (2 CAr), 134.1 (CAr),
133.8 (CAr), 131.3 (CAr), 130.2 (CAr), 128.8 (4 CAr), 128.5 (CAr), 128.0 (2
CAr), 127.5 (CAr), 127.4 (4 CAr), 126.7 (CAr), 125.3 (CAr), 124.8 (CAr),
124.7 (CAr), 70.1 (CH2OH), 69.8 (C).
IR (neat): 3222, 3049, 2952, 2922, 2859, 1639, 1510, 1460, 1257,
1030, 780, 728 cm–1
.
1H NMR (CDCl3, 400 MHz): δ = 8.26 (d, J = 8.0 Hz, 1 H, ArH), 7.93 (d, J =
8.2 Hz, 1 H, ArH), 7.88 (d, J = 8.7 Hz, 1 H, ArH), 7.60–7.51 (m, 3 H,
ArH), 7.46 (dd, J = 8.3, 7.0 Hz, 1 H, ArH), 5.93 (br s, 1 H, NH), 5.05 (br s,
1 H, OH), 3.87 (s, 2 H, CH2OH), 1.83–1.66 (m, 4 H, CH2C), 1.45–1.26
(m, 12 H, CH2), 0.90 (t, J = 6.8 Hz, 6 H, CH3).
13C NMR (CDCl3, 50 MHz): δ = 170.9 (C=O), 134.9 (CAr), 133.7 (CAr),
130.7 (CAr), 130.0 (CAr), 128.4 (CAr), 127.3 (CAr), 126.6 (CAr), 125.2 (CAr),
124.8 (CAr), 124.7 (CAr), 68.0 (CH2OH), 62.5 (C), 34.7 (2 CH2), 32.3 (2
CH2), 23.0 (2 CH2), 22.6 (2 CH2), 14.1 (2 CH3).
HRMS (ESI+): m/z [M + Na+] calcd for C25H21NNaO2: 390.1464; found:
390.1462.
HRMS (ESI+): m/z [M + Na+] calcd for C23H33NNaO2: 378.2404; found:
378.2394.
N-[2-Hydroxy-1,1-bis(4-methoxyphenyl)ethyl]-1-naphthamide
(2ig)
Purification by flash chromatography afforded 2ig.
N-(2-Benzyl-1-hydroxy-3-phenylpropan-2-yl)-1-naphthamide
Yield: 1.75 g (82%); yellow foam; mp 187 °C; Rf = 0.35 (petroleum
(2id)
ether–EtOAc, 70:30).
IR (neat): 3273, 2837, 1640, 1610, 1511, 1249, 1180, 1029, 781 cm–1
Purification by flash chromatography afforded 2id.
.
Yield: 1.60 g (81%); pale-yellow solid; mp 170–171 °C; Rf = 0.19 (pe-
troleum ether–EtOAc, 80:20).
1H NMR (CDCl3, 400 MHz): δ = 8.34 (d, J = 7.8 Hz, 1 H, ArH), 7.94 (d, J =
8.4 Hz, 1 H, ArH), 7.88 (dd, J = 7.9, 2.3 Hz, 1 H, ArH), 7.71 (dd, J = 7.1,
1.0 Hz, 1 H, ArH), 7.61–7.52 (m, 2 H, ArH), 7.47 (dd, J = 8.3, 7.1 Hz, 1 H,
ArH), 7.29 (dd, J = 6.7, 2.2 Hz, 4 H, ArH), 6.91 (dd, J = 6.7, 2.2 Hz, 4 H,
ArH), 6.87 (br s, 1 H, NH), 5.37 (br s, 1 H, OH), 4.52 (s, 2 H, CH2), 3.81
(s, 6 H, 2 CH3).
13C NMR (CDCl3, 100 MHz): δ = 170.3 (C=O), 159.1 (2 CAr), 134.3 (CAr),
134.2 (4 CAr), 133.8 (CAr), 131.2 (CAr), 130.1 (4 CAr), 128.5 (2 CAr), 127.5
(CAr), 126.7 (CAr), 125.3 (CAr), 124.8 (CAr), 124.6 (CAr), 114.0 (2 CAr), 70.3
(CH2), 69.0 (C), 55.3 (2 CH3).
IR (neat): 3411, 3348, 3083, 2940, 1632, 1537, 1316, 1074, 790,
704 cm–1
.
1H NMR (CDCl3, 400 MHz): δ = 8.25–8.23 (m, 1 H, ArH), 7.90–7.84 (m,
2 H, ArH), 7.52–7.50 (m, 2 H, ArH), 7.39–7.38 (m, 2 H, ArH), 7.30–7.26
(m, 10 H, ArH), 6.00 (br s, 1 H, NH), 3.82 (s, 2 H, CH2OH), 3.64 (br s,
1 H, OH), 3.41 (d, J = 13.7 Hz, 2 H, CH2Ph), 3.17 (d, J = 13.7 Hz, 2 H,
CH2Ph).
13C NMR (CDCl3, 100 MHz): δ = 170.6 (C=O), 136.6 (2 CAr), 134.6 (CAr),
133.8 (CAr), 130.9 (CAr), 130.7 (4 CAr), 130.0 (CAr), 128.6 (4 CAr), 128.4
(CAr), 127.3 (CAr), 127.0 (2 CAr), 126.5 (CAr), 125.3 (CAr), 125.0 (CAr),
124.7 (CAr), 66.5 (CH2OH), 61.9 (C), 41.0 (2 CH2Ph).
HRMS (ESI+): m/z [M + H+] calcd for C27H26NO4: 428.1845; found:
428.1856.
HRMS (ESI+): m/z [M + H+] calcd for C27H26NO2: 396.1964; found:
396.1966.
N-[3-(Hydroxymethyl)penta-1,4-dien-3-yl]-1-naphthamide (2ih)
Purification by flash chromatography afforded 2ih.
Yield: 949 mg (71%); pale-yellow solid; mp 74 °C; Rf = 0.13 (petro-
N-[4-(Hydroxymethyl)-1,7-diphenylheptan-4-yl]-1-naphthamide
leum ether–EtOAc, 80:20).
(2ie)
Purification by flash chromatography afforded 2ie.
IR (neat): 3338, 3171, 3052, 1632, 1510, 1259, 780 cm–1
.
Yield: 1.78 g (79%); white solid; mp 94 °C; Rf = 0.19 (petroleum ether–
EtOAc, 80:20).
1H NMR (CDCl3, 400 MHz): δ = 8.34 (d, J = 7.9 Hz, 1 H, ArH), 7.95 (d, J =
8.5 Hz, 1 H, ArH), 7.89 (dd, J = 7.8, 1.9 Hz, 1 H, ArH), 7.68 (dd, J = 6.9,
1.4 Hz, 1 H, ArH), 7.60–7.52 (m, 2 H, ArH), 7.48 (dd, J = 8.4, 7.0 Hz, 1 H,
IR (neat): 3219, 3055, 2970, 2880, 1634, 1554, 1339, 1252, 1062,
786 cm–1
.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, 906–916