4 Experimental Data
51
2.1z 2-Amino-4-phenyl-1-(pyrrolidin-1-yl)butan-1-one
To 32 mg (0.077 mmol) 1d in 0.5 mL MeCN 25.3 mg (0.23 mmol) thiophenol and
42.4 mg (0.307 mmol) freshly ground K2CO3 was added. The mixture was heated
to 50 °C for 40 h. Then, the solvent was removed under reduced pressure and the
crude product was purified by column chromatography on silica gel
(EtOAc:(99% MeOH, 1% NH4OH) = 9:1) to yield amine 1z (16.6 mg, 93%) as a
pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 7.31–7.25 (m, 2H
Ar
), 7.23–7.16 (m, 3H
Ar
),
3.54–3.37 (m, 3H
1,7
), 3.34–3.26 (m, 1H
10
), 3.19–3.10 (m, 1H
10
), 2.86–2.67 (m,
2H
11
), 1.96–1.62 (m, 8H
NH,3,8,9
), ppm;
13
C NMR (100 MHz, CDCl3): δ = 174.1
(C
2
), 141.7 (C
12
), 128.7 (2CH
Ar
), 128.6 (2CH
Ar
), 126.1 (CH
15
), 52.4 (CH
1
), 46.1
(CH2
7
), 46.0 (CH2
10
), 36.9 (CH2
Alk
), 32.2 (CH2
Alk
), 26.2 (CH2
Alk
), 24.2 (CH2
Alk
)
ppm; IR (neat):
= 3363, 3060, 3025, 2950, 2873, 1631, 1449, 1370, 1342, 752,
701 cm
-1
; HRMS (ESI): m/z calculated for [M+H]
+
(C14H21N2O) 233.1648, found
233.1647.
2.2a 2-(4-Nitrophenoxy)-4-phenyl-1-(pyrrolidin-1-yl)butan-1-one
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:1) yielded the product
(56.0 mg, 79%) as a pale yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 8.16 (d, J = 9.3 Hz, 2H
25,27
), 7.29–7.12 (m,
5H
Ar
), 6.87 (d, J = 9.3 Hz, 2H
24,28
), 4.66 (dd, J = 9.1, 4.0 Hz, 1H
1
), 3.53–3.37 (m,