50
4 Experimental Data
2.1y Methyl 9-((R)-2-benzhydrylpyrrolidin-1-yl)-8-((N,4-dimethylphenyl)sulfonamido)-9-oxononanoate
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:5–1:2) yielded the product
(34.4 mg, 28%) as a white solid. Isolated as a mixture of diasteromers in a ratio of
1:1.3, only the major one is reported for the
1
H NMR. Both diastereomers are reported for the
13
C NMR (maj = major, min = minor) and the IR.
1
H NMR (700 MHz, CDCl3): δ = 7.62 (d, J = 8.3 Hz, 2H
24,28
), 7.48–7.12 (m,
12H
Ar
), 5.51 (dd, J = 10.8, 6.1 Hz, 1H
9
), 4.06 (t, J = 7.1 Hz, 1H
1
), 3.91–3.58 (m,
2H
6,18
), 3.68 (s, 3H
17
), 3.50 (m, 1H
6
), 2.62 (s, 3H
11
), 2.42 (s, 3H
29
), 2.25 (t, J = 7.4
Hz, 2H
13
), 2.00–1.85 (m, 4H
7,8
), 1.51–1.47 (m, 2H
12
), 1.20–0.78 (m, 5H
Alk
), 0.65–
0.59 (m, 1H
Alk
), 0.46–0.39 (m, 1H
Alk
), 0.30–0.23 (m, 1H
Alk
) ppm.
13
C NMR (175
MHz, CDCl3): 174.3 (C
14
), 168.3 (C
2,maj
), 168.0 (C
2,min
), 143.7 (C
21
), 143.6 (C
21
),
142.2 (C
Ar
), 142.1 (C
Ar
), 142.1 (C
Ar
), 141.6 (C
Ar
), 136.4 (C
26
), 129.8 (2C
Ar
), 129.8
(2C
Ar
), 129.5 (2C
Ar
), 129.4 (2C
Ar
), 129.1 (2C
Ar
), 129.0 (2C
Ar
), 129.0 (2C
Ar
), 128.7
(2C
Ar
), 128.6 (2C
Ar
), 128.2 (2C
Ar
), 127.5 (2C
Ar
), 127.5 (2C
Ar
), 127.0 (C
Ar
), 126.9
(C
Ar
), 126.8 (C
Ar
), 126.3 (C
Ar
), 60.8 (CH
9,maj
), 60.2 (CH
min
), 57.6 (CH
min
), 57.1
(CH
1,maj
), 54.8 (CH
18,maj
), 52.9 (CH
min
), 51.6 (CH3
17
), 46.9 (CH2
min
), 44.8
(CH2
6,maj
), 34.2 (CH2
13,maj
), 34.1 (CH2
13,min
), 30.3 (CH2
Alk
), 30.0 (CH3
11,maj
), 29.9
(CH3
11,min
), 29.2 (CH2
Alk
), 29.1 (CH2
Alk
), 29.0 (CH2
Alk
), 27.9 (CH2
Alk
), 26.9
(CH2
Alk
), 26.9 (CH2
Alk
), 26.4 (CH2
Alk
), 25.6 (CH2
Alk
), 25.0 (CH2
Alk
), 24.9 (CH2
Alk
),
23.6 (CH2
Alk
), 21.9 (CH3
29,min
), 21.7 (CH3
29,maj
), 21.1 (CH2
Alk
) ppm. IR (neat):
= 3056, 3028, 2927, 2856, 1733, 1634, 1599, 1493, 1434, 1336, 1265, 1159, 1087,
814, 732 cm
-1
; HRMS (ESI): m/z calculated for [M+Na]
+
(C35H44N2O5SNa)
627.2863, found 627.2862.
4 Experimental Data
2.1y Methyl 9-((R)-2-benzhydrylpyrrolidin-1-yl)-8-((N,4-dimethylphenyl)sulfonamido)-9-oxononanoate
The product was prepared according to general procedure C. Purification by column chromatography on silica gel (EtOAc:heptane = 1:5–1:2) yielded the product
(34.4 mg, 28%) as a white solid. Isolated as a mixture of diasteromers in a ratio of
1:1.3, only the major one is reported for the
1
H NMR. Both diastereomers are reported for the
13
C NMR (maj = major, min = minor) and the IR.
1
H NMR (700 MHz, CDCl3): δ = 7.62 (d, J = 8.3 Hz, 2H
24,28
), 7.48–7.12 (m,
12H
Ar
), 5.51 (dd, J = 10.8, 6.1 Hz, 1H
9
), 4.06 (t, J = 7.1 Hz, 1H
1
), 3.91–3.58 (m,
2H
6,18
), 3.68 (s, 3H
17
), 3.50 (m, 1H
6
), 2.62 (s, 3H
11
), 2.42 (s, 3H
29
), 2.25 (t, J = 7.4
Hz, 2H
13
), 2.00–1.85 (m, 4H
7,8
), 1.51–1.47 (m, 2H
12
), 1.20–0.78 (m, 5H
Alk
), 0.65–
0.59 (m, 1H
Alk
), 0.46–0.39 (m, 1H
Alk
), 0.30–0.23 (m, 1H
Alk
) ppm.
13
C NMR (175
MHz, CDCl3): 174.3 (C
14
), 168.3 (C
2,maj
), 168.0 (C
2,min
), 143.7 (C
21
), 143.6 (C
21
),
142.2 (C
Ar
), 142.1 (C
Ar
), 142.1 (C
Ar
), 141.6 (C
Ar
), 136.4 (C
26
), 129.8 (2C
Ar
), 129.8
(2C
Ar
), 129.5 (2C
Ar
), 129.4 (2C
Ar
), 129.1 (2C
Ar
), 129.0 (2C
Ar
), 129.0 (2C
Ar
), 128.7
(2C
Ar
), 128.6 (2C
Ar
), 128.2 (2C
Ar
), 127.5 (2C
Ar
), 127.5 (2C
Ar
), 127.0 (C
Ar
), 126.9
(C
Ar
), 126.8 (C
Ar
), 126.3 (C
Ar
), 60.8 (CH
9,maj
), 60.2 (CH
min
), 57.6 (CH
min
), 57.1
(CH
1,maj
), 54.8 (CH
18,maj
), 52.9 (CH
min
), 51.6 (CH3
17
), 46.9 (CH2
min
), 44.8
(CH2
6,maj
), 34.2 (CH2
13,maj
), 34.1 (CH2
13,min
), 30.3 (CH2
Alk
), 30.0 (CH3
11,maj
), 29.9
(CH3
11,min
), 29.2 (CH2
Alk
), 29.1 (CH2
Alk
), 29.0 (CH2
Alk
), 27.9 (CH2
Alk
), 26.9
(CH2
Alk
), 26.9 (CH2
Alk
), 26.4 (CH2
Alk
), 25.6 (CH2
Alk
), 25.0 (CH2
Alk
), 24.9 (CH2
Alk
),
23.6 (CH2
Alk
), 21.9 (CH3
29,min
), 21.7 (CH3
29,maj
), 21.1 (CH2
Alk
) ppm. IR (neat):
= 3056, 3028, 2927, 2856, 1733, 1634, 1599, 1493, 1434, 1336, 1265, 1159, 1087,
814, 732 cm
-1
; HRMS (ESI): m/z calculated for [M+Na]
+
(C35H44N2O5SNa)
627.2863, found 627.2862.