E
Q. Li et al.
Paper
Synthesis
1H NMR (500 MHz, CDCl3): = 5.56 (s, 1 H), 2.06–1.97 (m, 2 H), 1.57–
1.45 (m, 2 H), 1.27 (s, 9 H), 1.24–1.16 (m, 8 H), 0.81 (t, J = 6.9 Hz, 3 H).
13C NMR (125 MHz, CDCl3): = 172.51, 50.74, 37.46, 31.54, 29.02,
28.89, 28.64, 25.68, 22.42, 13.87.
The spectroscopic data matched those reported.13d
N-(tert-Butyl)-5-phenoxypentanamide (3k)
Yield: 96% (47.9 mg); white solid; mp 91–93 °C.
1H NMR (500 MHz, CDCl3): = 7.30–7.24 (m, 2 H), 6.96–6.91 (m, 1 H),
6.90–6.86 (m, 2 H), 5.52 (s, 1 H), 3.96 (t, J = 5.9 Hz, 2 H), 2.20–2.13 (m,
2 H), 1.83–1.76 (m, 4 H), 1.34 (s, 9 H).
13C NMR (125 MHz, CDCl3): = 171.97, 158.84, 129.32, 120.50,
N-(tert-Butyl)tridecanamide (3f)
114.38, 67.41, 50.96, 37.01, 28.73, 28.58, 22.42.
HRMS (ESI): m/z [M + H]+ calcd for C15H24NO2+: 250.18015; found:
Yield: 85% (45.8 mg); white solid; mp 48–50 °C.
1H NMR (500 MHz, CDCl3): = 5.38 (s, 1 H), 2.09–2.02 (m, 2 H), 1.62–
1.52 (m, 2 H), 1.32 (s, 9 H), 1.29–1.20 (m, 18 H), 0.86 (t, J = 6.9 Hz,
3 H).
250.17957.
N-(tert-Butyl)-5-(4-fluorophenoxy)pentanamide (3l)
13C NMR (125 MHz, CDCl3): = 172.53, 50.90, 37.65, 31.85, 29.59,
Yield: 87% (46.5 mg); white solid; mp 93–94 °C.
1H NMR (500 MHz, CDCl3): = 6.95–6.88 (m, 2 H), 6.81–6.76 (m, 2 H),
5.53 (s, 1 H), 3.89 (s, 2 H), 2.14 (t, J = 6.7 Hz, 2 H), 1.79–1.72 (m, 4 H),
1.32 (s, 9 H).
29.57, 29.55, 29.45, 29.33, 29.28, 29.17, 28.77, 25.76, 22.62, 14.04.
The spectroscopic data matched those reported.6
1
N-(tert-Butyl)-4-phenylbutanamide (3g)
13C NMR (125 MHz, CDCl3): = 171.89, 157.02 (d, JC–F = 237.9 Hz),
4
2
3
155.00 (d, JC–F = 2.0 Hz), 115.60 (d, JC–F = 23.0 Hz), 115.31 (d, JC–F
=
Yield: 90% (39.5 mg); white solid; mp 65–67 °C.
8.0 Hz), 68.14, 50.95, 36.95, 28.70, 28.60, 22.31.
1H NMR (500 MHz, CDCl3): = 7.32–7.27 (m, 2 H), 7.23–7.16 (m, 3 H),
5.29 (s, 1 H), 2.65 (t, J = 7.5 Hz, 2 H), 2.10 (t, J = 7.5 Hz, 2 H), 1.99–1.91
(m, 2 H), 1.35 (s, 9 H).
HRMS (ESI): m/z [M + Na]+ calcd for C15H22FNNaO2+: 290.15268;
found: 290.15159.
13C NMR (125 MHz, CDCl3): = 171.95, 141.57, 128.40, 128.25,
125.80, 50.94, 36.63, 35.03, 28.73, 27.08.
N-(tert-Butyl)-5-(4-chlorophenoxy)pentanamide (3m)
Yield: 83% (52.8 mg); white solid; mp 104–106 °C.
The spectroscopic data matched those reported.6
1H NMR (500 MHz, CDCl3): = 7.21–7.15 (m, 2 H), 6.81–6.74 (m, 2 H),
5.53 (s, 1 H), 3.89 (t, J = 5.7 Hz, 2 H), 2.14 (t, J = 6.9 Hz, 2 H), 1.79–1.70
(m, 4 H), 1.31 (s, 9 H).
13C NMR (125 MHz, CDCl3): = 171.85, 157.46, 129.11, 125.21,
115.63, 67.80, 50.94, 36.89, 28.69, 28.48, 22.24.
N-(tert-Butyl)-6-fluorohexanamide (3h)
Yield: 78% (29.5 mg); yellow oil.
1H NMR (500 MHz, CDCl3): = 5.48 (s, 1 H), 4.40 (dt, J = 47.3, 6.1 Hz,
2 H), 2.07 (t, J = 7.5 Hz, 2 H), 1.72–1.57 (m, 4 H), 1.43–1.34 (m, 2 H),
1.30 (s, 9 H).
The spectroscopic data matched those reported.6
13C NMR (125 MHz, CDCl3): = 172.08, 83.78 (d, JC–F = 164.2 Hz),
1
5-(4-Bromophenoxy)-N-(tert-butyl)pentanamide (3n)
2
3
50.90, 37.21, 30.04 (d, JC–F = 19.6 Hz), 28.67, 25.18, 24.70 (d, JC–F
=
Yield: 86% (56.5 mg); white solid; mp 103–105 °C.
5.4 Hz).
1H NMR (500 MHz, CDCl3): = 7.36–7.30 (m, 2 H), 6.77–6.71 (m, 2 H),
5.44 (s, 1 H), 3.91 (t, J = 5.9 Hz, 2 H), 2.17–2.12 (m, 2 H), 1.80–1.74 (m,
4 H), 1.33 (s, 9 H).
HRMS (ESI): m/z [M + H]+ calcd for C10H21FNO+: 190.16017; found:
190.15942.
N-(tert-Butyl)-7-chloroheptanamide (3i)
13C NMR (125 MHz, CDCl3): = 171.82, 157.99, 132.11, 116.21,
112.58, 67.79, 51.02, 36.96, 28.75, 28.52, 22.27.
HRMS (ESI): m/z [M + Na]+ calcd for C15H22BrNNaO2+: 350.07261;
found: 350.07150.
Yield: 68% (29.9 mg); yellow oil.
1H NMR (500 MHz, CDCl3): = 5.36 (s, 1 H), 3.53 (t, J = 6.7 Hz, 2 H),
2.09 (t, J = 7.5 Hz, 2 H), 1.81–1.73 (m, 2 H), 1.66–1.58 (m, 2 H), 1.49–
1.42 (m, 2 H), 1.36–1.31 (m, 11 H).
N-(tert-Butyl)-5-(4-formylphenoxy)pentanamide (3o)
13C NMR (125 MHz, CDCl3): = 172.21, 51.02, 44.97, 37.39, 32.34,
Yield: 91% (50.5 mg); white solid; mp 92–93 °C.
28.80, 28.33, 26.52, 25.45.
1H NMR (500 MHz, CDCl3): = 9.82 (s, 1 H), 7.85–7.73 (m, 2 H), 6.99–
6.91 (m, 2 H), 5.49 (s, 1 H), 4.03 (t, J = 5.5 Hz, 2 H), 2.17 (t, J = 6.8 Hz,
2 H), 1.80 (dt, J = 11.8, 4.8 Hz, 4 H), 1.33 (s, 9 H).
13C NMR (125 MHz, CDCl3): = 190.76, 171.81, 164.02, 131.92,
129.73, 114.68, 67.97, 51.07, 36.88, 28.75, 28.43, 22.17.
The spectroscopic data matched those reported.6
7-(tert-Butylamino)-7-oxoheptyl 4-Methylbenzenesulfonate (3j)
Yield: 70% (49.8 mg); yellow oil.
1H NMR (500 MHz, CDCl3): = 7.78 (d, J = 8.3 Hz, 2 H), 7.35 (d, J =
8.2 Hz, 2 H), 5.29 (s, 1 H), 4.01 (t, J = 6.4 Hz, 2 H), 2.45 (s, 3 H), 2.05 (t,
J = 7.5 Hz, 2 H), 1.66–1.61 (m, 2 H), 1.58–1.52 (m, 2 H), 1.34–1.33 (m,
9 H), 1.30–1.20 (m, 4 H).
HRMS (ESI): m/z [M + H]+ calcd for C16H24NO3+: 278.17507; found:
278.17468.
5-(4-Acetylphenoxy)-N-(tert-butyl)pentanamide (3p)
13C NMR (125 MHz, CDCl3): = 172.19, 144.69, 133.18, 129.82,
Yield: 86% (50.1 mg); white solid; mp 87–89 °C.
127.84, 70.55, 51.06, 37.34, 28.82, 28.63, 28.43, 25.36, 25.09, 21.61.
1H NMR (500 MHz, CDCl3): = 7.89 (d, J = 8.9 Hz, 2 H), 6.88 (d, J =
8.9 Hz, 2 H), 5.50 (s, 1 H), 4.01 (t, J = 5.5 Hz, 2 H), 2.52 (s, 3 H), 2.16 (t,
J = 6.9 Hz, 2 H), 1.84–1.75 (m, 4 H), 1.33 (s, 9 H).
HRMS (ESI): m/z [M + H]+ calcd for C18H30NO4S+: 356.18901; found:
356.18823.
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