54
4 Experimental Data
The product was prepared according to general procedure D from amide 2.1b (63
mg, 0.15 mmol). Purification by column chromatography on silica gel
(EtOAc:heptane = 1:1) yielded the product (24.0 mg, 45%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 8.21 (d, J = 9.0 Hz, 2H
9,11
), 7.57 (d, J =
9.0 Hz, 2H
8,12
), 7.25–7.20 (m, 2H
Ar
), 7.19–7.13 (m, 1H
23
), 7.12–7.06 (m, 2H
Ar
),
3.53 (bs, 2H
Alk
), 3.19 (bs, 1H
Alk
), 2.70 (bs, 1H
Alk
), 2.62–2.53 (m, 1H
Alk
), 2.42–2.33
(m, 2H
Alk
), 2.28 (s, 3H
13
), 1.78–1.49 (m, 4H
Alk
) ppm;
13
C NMR (150 MHz,
CDCl3): δ = 170.6 (C
18
), 150.0 (C
Ar
), 147.0 (C
Ar
), 141.7 (C
Ar
), 128.5 (2CH
Ar
),
128.4 (2CH
Ar
), 127.3 (2CH
Ar
), 126.1 (CH
23
), 123.8 (2CH
Ar
), 68.5 (C
19
), 47.8
(CH2
1
), 46.6 (CH2
4
), 35.4 (CH2
Alk
), 29.4 (CH2
Alk
), 29.2 (CH2
13
), 26.8 (CH3
Alk
), 23.2
(CH2
Alk
) ppm; IR (neat):
= 2946, 2876, 2798, 1625, 1603, 1519, 1401, 1346,
1109, 854 cm
-1
; HRMS (ESI): m/z calculated for [M+H]
+
(C21H26N3O3) 368.1969,
found 368.1971.
2.3b 2-(Methylamino)-2-(4-nitrophenyl)-3-phenyl-1-(pyrrolidin-1-yl)propan-1-one
The product was prepared according to general procedure D from amide 2.1t
(417.5 mg, 1 mmol). Purification by column chromatography on silica gel
(EtOAc:heptane = 3:2) yielded the product (159.0 mg, 45%) as a pale yellow solid.