4 Experimental Data
55
1
H NMR (600 MHz, CDCl3): δ = 8.10 (d, J = 9.0 Hz, 2H
9,11
), 7.31–7.24 (m,
2H
Ar
), 7.14–7.06 (m, 3H
Ar
), 6.52 (d, J = 9.0 Hz, 2H
8,12
), 3.71 (d, J = 14.3 Hz,
1H
20
), 3.67–3.62 (m, 1H
1
), 3.60–3.49 (m, 2H
1,4
), 3.24 (d, J = 14.3 Hz, 1H
20
), 2.49
(s, 3H
13
), 2.34–2.36 (m, 1H
4
), 1.79–1.52 (m, 4H
2,3
), ppm;
13
C NMR (150 MHz,
CDCl3): δ = 169.8 (C
18
), 149.8 (C
Ar
), 146.7 (C
26
), 135.9 (C
Ar
), 130.4 (CH
Ar
), 128.1
(CH
Ar
), 127.2 (CH
Ar
), 126.8 (CH
Ar
), 123.3 (CH
Ar
), 69.53 (C
19
), 47.6 (CH2
1
), 46.4
(CH2
4
), 41.1 (CH2
Alk
), 30.1 (CH3
13
), 26.7 (CH2
Alk
), 23.3 (CH2
Alk
) ppm; IR (neat):
= 3028, 2947, 2875, 2802, 1629, 1599, 1518, 1451, 1398, 1345, 1107, 850,
705 cm
-1
; HRMS (ESI): m/z calculated for [M+H]
+
(C20H24N3O3) 354.1812,
found 354.1816.
2.3c N,N-Dimethyl-2-(methylamino)-2-(4-nitrophenyl)-4-phenylbutanamide
The product was prepared according to general procedure D from amide 2.1s (39
mg, 0.096 mmol). Purification by column chromatography on silica gel
(EtOAc:heptane = 1:2) yielded the product (17.0 mg, 51%) as a colourless liquid.
1
H NMR (400 MHz, CDCl3): δ = 8.23 (d, J = 9.0 Hz, 2H
9,11
), 7.53 (d, J =
9.0 Hz, 2H
8,12
), 7.26–7.20 (m, 2H
Ar
), 7.19–7.13 (m, 1H
23
), 7.10–7.04 (m, 2H
Ar
),
2.91 (bs, 3H
1
), 2.73 (bs, 3H
4
), 2.65–2.53 (m, 1H
Alk
), 2.39–2.26 (m, 2H
21
), 2.30 (s,
3H
13
), 2.25–2.12 (m, 1H
20
), 1.97 (bs, 1H
NH
) ppm;
13
C NMR (100 MHz, CDCl3):
δ = 171.7 (C
18
), 150.4 (C
Ar
), 146.9 (C
Ar
), 141.6 (C
Ar
), 128.6 (2CH
Ar
), 128.4
(2CH
Ar
), 126.8 (2CH
Ar
), 126.1 (CH
23
), 123.9 (2CH
Ar
), 68.5 (C
19
), 37.6 (CH2
Alk
),
36.5 (CH2
1,4
), 29.5 (CH2
Alk
), 29.4 (CH2
13
) ppm; IR (neat):
= 2928, 2857, 1666,
1634, 1601, 1518, 1385, 1345, 1256, 1091, 855, 701, 659 cm
-1
; HRMS (ESI): m/z
calculated for [M+H]
+
(C19H24N3O3) 342.1813, found 342.1813.