4 Experimental Data
53
2.2o 1-(Dimethylamino)-1-oxopentan-2-yl formate
The product was prepared according to general procedure C with the difference
that no sulfonamide or alcohol was added. Purification by column chromatography
on silica gel (EtOAc:heptane = 1:1) yielded the product (21.1 mg, 26%) as a pale
yellow liquid.
1
H NMR (400 MHz, CDCl3): δ = 8.08 (s, 1H
8
), 5.40 (dd, J = 4.3, 8.6 Hz,
1H
1
), 3.08 (s, 3H
10
), 3.96 (s, 3H
11
), 1.91–1.80 (m, 1H
3
), 1.77–1.66 (m, 1H
3
), 1.56–
1.35 (m, 2H
7
), 0.95 (t, J = 7.3 Hz, 3H
12
) ppm;
13
C NMR (175 MHz, CDCl3): δ =
169.4 (C
2
), 160.7 (CH
8
), 69.9 (CH
1
), 37.0 (CH3
10
), 36.1 (CH3
10
), 33.1 (CH2
3
), 18.6
(CH2
7
), 13.8 (CH3
10
) ppm; IR (neat):
= 2960, 2934, 2874, 1720, 1652, 1500,
1462, 1402, 1259, 1163, 1108, 1059, 852, 631 cm
-1
; HRMS (ESI): m/z calculated
for [M+Na]
+
(C8H15NO3Na) 196.0944, found 196.0942.
2.2p 2-Hydroxy-N,N-dimethylpentanamide
The product was prepared according to general procedure C with the difference
that no sulfonamide or alcohol was added. Purification by column chromategraphy
(EtOAc:heptane = 1:1) yielded the product (36.3 mg, 42%) as a pale yellow liquid.
All spectroscopic properties are in good accordance with reported data.
[51]
General procedure D for the synthesis of -arylated amides 2.3a–c
To a solution of the amide (1 eq.) in MeCN (0.1 M) was added tetrapropyl ammonium hydroxide (40% (aq.), 2 eq.) The solution was stirred for 16 h. Then it was
washed with saturated NH4Cl solution and brine. The organic layer was dried with
MgSO4, the solvent evaporated and the crude product purified by column chromatography on silica gel.
2.3a 2-(Methylamino)-2-(4-nitrophenyl)-4-phenyl-1-(pyrrolidin-1-yl)butan-1-one