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23.9, 22.9, 21.5. Spectral data was consistent with N-(4-tolue- MHz, CDCl3) d 145.7, 144.7, 142.8, 135.6, 129.4, 128.4, 127.0,
nesulfonyl)-2-methylpyrrolidine.29
126.6, 126.5, 126.5, 126.4, 126.2, 61.1, 58.6, 52.3, 42.4, 28.2,
N-(p-Toluenesulfonyl)-3-methyl-2-azaspiro[4.5]decane 2f. 21.4, 10.0. IR: 3056, 3025, 2946, 2929, 2879, 1949, 1806, 1598,
Compound 2f was prepared according to the general proce- 1494, 1448, 1334, 1262, 1093, 1026, 804 cmꢁ1. HRMS-ESI (m/
dure and was isolated as a yellow oil (300 mg, 97% yield) aer z): [M + H]+ calcd for C25H27NO2S, 406.1841; found: 406.1842.
ash chromatography (EtOAc/petroleum 5%). 1H NMR (400
N-(4,4-Dimethyl-1-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl-
MHz, CDCl3) d 7.64 (d, J ¼ 8.1 Hz, 2H), 7.22 (d, J ¼ 7.9 Hz, 2H), methyl)-4-methyl-benzenesulfonamide 2j. Compound 2j was
3.51–3.43 (m, 1H), 3.16 (d, J ¼ 10.6 Hz, 1H), 3.06 (d, J ¼ 10.7 prepared according to the general procedure and was isolated as
Hz, 1H), 2.33 (s, 3H), 1.71 (dd, J ¼ 12.7, 7.1 Hz, 1H), 1.32 (d, a white solid (400 mg, 95% yield) aer ash chromatography
J ¼ 6.1 Hz, 3H), 1.26–1.04 (m, 8H), 0.79–0.70 (m, 2H), 0.61 (dd, (EtOAc/petroleum 10%); mp 148–150 ꢀC. 1H NMR (400 MHz,
J ¼ 11.6, 5.4 Hz, 1H). 13C NMR (100 MHz, CDCl3) d 143.3, CDCl3) d 7.61 (d, J ¼ 8.2 Hz, 2H), 7.38 (d, J ¼ 7.9 Hz, 1H), 7.24–
135.0, 129.5, 127.3, 55.1, 40.9, 36.5, 34.2, 25.8, 23.7, 22.8, 22.7, 7.06 (m, 6H), 6.99 (t, J ¼ 7.1 Hz, 1H), 6.82 (d, J ¼ 7.3 Hz, 2H), 6.64
21.5. Spectral data was consistent with N-(p-toluenesulfonyl)- (d, J ¼ 7.8 Hz, 1H), 4.05 (d, J ¼ 9.5 Hz, 1H), 3.64 (t, J ¼ 11.2 Hz,
3-methyl-2-azaspiro[4.5]decane.15
1H), 3.26 (dd, J ¼ 11.9, 1.8 Hz, 1H), 2.42 (ddd, J ¼ 13.6, 10.8, 5.4
2-Isopropyl-4,4-dimethyl-1-(toluene-4-sulfonyl)-pyrrolidine 2g. Hz, 1H), 2.35 (s, 3H), 1.77 (dt, J ¼ 7.5, 3.5 Hz, 1H), 1.36–1.33 (m,
Compound 2g was prepared according to the general procedure 2H), 1.22 (s, 3H), 1.17 (s, 3H). 13C NMR (100 MHz, CDCl3) d
and was isolated as a white solid (293 mg, 99% yield) aer ash 148.7, 147.1, 143.4, 136.3, 136.0, 129.7, 128.1, 127.8, 127.4,
chromatography (EtOAc/petroleum 10%); mp 83–85 ꢀC. 1H NMR 127.3, 127.2, 127.1, 126.4, 126.2, 51.7, 47.6, 34.1, 33.8, 31.9, 31.8,
(400 MHz, CDCl3) d 7.65 (d, J ¼ 8.1 Hz, 2H), 7.22 (d, J ¼ 8.0 Hz, 31.5, 21.5. IR: 3296, 3057, 3019, 2959, 2916, 2860, 1931, 1807,
2H), 3.63–3.58 (m, 1H), 3.19 (d, J ¼ 10.8 Hz, 1H), 2.94 (d, J ¼ 10.9 1598, 1490, 1424, 1328, 1162, 1093, 849, 757, 702, 669. IR: 3296,
Hz, 1H), 2.45–2.43 (m, 1H), 2.35 (s, 3H), 1.43–1.36 (m, 2H), 0.92 (s, 3057, 3019, 2959, 2916, 2860, 1931, 1807, 1598, 1490, 1424, 1328,
3H), 0.75 (dd, J ¼ 10.8, 6.9 Hz, 6H), 0.40 (s, 3H). 13C NMR 1162, 1093, 849, 757, 702, 669. HRMS-ESI (m/z): [M + H]+ calcd
(100 MHz, CDCl3) d 142.9, 136.2, 129.4, 127.2, 64.8, 61.8, 39.2, for C26H29NO2S, 420.1997; found: 420.1994.
37.1, 30.2, 26.1, 25.7, 21.5, 19.2, 14.5. HRMS-ESI (m/z): [M + H]+
calcd for C16H25NO2S, 296.1684; found: 296.1674.
Crystal data for 2j. C26H29NO2S, M ¼ 419.56, triclinic, a ¼
ꢀ
˚
˚
˚
11.089(2) A, b ¼ 13.375(3) A, c ¼ 16.281(3) A, a ¼ 80.22(3) , b ¼
3
ꢀ
ꢀ
˚
3-Isopropyl-2-(toluene-4-sulfonyl)-2-aza-spiro[4.5]decane 2h. 77.60(3) , g ¼ 77.15(3) , V ¼ 2280.3(8) A , T ¼ 293(2) K, space
Compound 2h was prepared according to the general procedure group P1, Z ¼ 4, m(MoKa) ¼ 0.164 mmꢁ1, 28 896 reections
ꢀ
and was isolated as a white solid (310 mg, 92% yield) aer ash measured, 10 801 independent reections (Rint ¼ 0.0359). The
chromatography (EtOAc/petroleum 10%); mp 103–105 ꢀC. 1H nal R1 values were 0.0540 (I > 2s(I)). The nal wR(F2) values
NMR (400 MHz, CDCl3) d 7.64 (d, J ¼ 8.1 Hz, 2H), 7.21 (d, J ¼ 8.0 were 0.1309 (I > 2s(I)). The nal R1 values were 0.0868 (all data).
Hz, 2H), 3.53–3.48 (m, 1H), 3.40 (d, J ¼ 11.2 Hz, 1H), 2.86 (d, J ¼ The nal wR(F2) values were 0.1512 (all data). The goodness of
11.2 Hz, 1H), 2.43–2.40 (m, 1H), 2.33 (s, 3H), 1.35–1.14 (m, 10H), t on F2 was 1.018.16
0.75 (dd, J ¼ 14.2, 6.9 Hz, 6H), 0.68–0.62 (m, 1H), 0.57–0.53 (m,
2-Methyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole 2l.
1H). 13C NMR (100 MHz, CDCl3) d 142.8, 135.8, 129.3, 127.0, Compound 2l was prepared according to the general proce-
63.8, 40.8, 36.3, 33.5, 30.2, 25.7, 23.7, 22.5, 21.3, 19.1, 14.4. IR: dure and was isolated as a white solid (140 mg, 48% yield)
3044, 2946, 2929, 2852, 2674, 2490, 1922, 1812, 1597, 1491, aer ash chromatography (EtOAc/petroleum 5%); mp 63–64
1449, 1340, 1158, 1092, 1036, 816, 730, 660 cmꢁ1. HRMS-ESI ꢀC, lit.28 1H NMR (400 MHz, CDCl3) d 7.56 (d, J ¼ 8.1 Hz, 1H),
(m/z): [M + H]+ calcd for C19H29NO2S, 336.1997; found: 7.46 (d, J ¼ 8.1 Hz, 2H), 7.10 (t, J ¼ 7.6 Hz, 1H), 7.06 (d, J ¼ 8.1
336.1998.
Hz, 2H), 6.93 (dt, J ¼ 14.5, 7.2 Hz, 2H), 4.28–4.23 (m, 1H), 2.79
Crystal data for 2h. C19H29NO2S, M ¼ 335.49, orthorhombic, (dd, J ¼ 16.0, 9.4 Hz, 1H), 2.33 (dt, J ¼ 13.1, 6.5 Hz, 1H), 2.24
a ¼ 9.2889(19) A, b ¼ 17.158(3) A, c ¼ 11.652(2) A, a ¼ 90.00 , (s, 3H), 1.32 (d, J ¼ 6.5 Hz, 3H). 13C NMR (100 MHz, CDCl3) d
ꢀ
˚
˚
˚
3
ꢀ
ꢀ
˚
b ¼ 90.00 , g ¼ 90.00 , V ¼ 1857.1(6) A , T ¼ 293(2) K, space 143.6, 140.9, 135.1, 131.5, 129.4, 127.5, 126.8, 125.2, 124.4,
group Pna2(1), Z ¼ 4, m(MoKa) ¼ 0.184 mmꢁ1, 17 703 reections 117.0, 58.3, 36.0, 23.3, 21.4. Spectral data was consistent with
measured, 4426 independent reections (Rint ¼ 0.0518). The 2-methyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indole.30
nal R1 values were 0.0441 (I > 2s(I)). The nal wR(F2) values
were 0.0986 (I > 2s(I)). The nal R1 values were 0.0585 (all data).
General procedure for intermolecular hydroamination
The nal wR(F2) values were 0.1084 (all data). The goodness of
t on F2 was 0.979. Flack parameter ¼ 0.00(7).16
A sealed tube was charged dry with alkene (2.00 mmol),
N-(p-Toluenesulfonyl)-2-ethyl-4,4-diphenylpyrrolidine 2i. 1,2-dichloroethane (10 mL), sulfonamide (4.0 mmol) and
Compound 2i was prepared according to the general proce- BF3$Et2Oꢀ(6.0 mmol). The tube was sealed and heated in an oil
dure and was isolated as a thick paste (140 mg, 34% yield) bath (60 C). The reaction mixture was stirred at this tempera-
1
aer ash chromatography (EtOAc/petroleum 5%). H NMR ture for 24 h and was then cooled to room temperature. The
(400 MHz, CDCl3) 7.50 (d, J ¼ 8.2 Hz, 2H), 7.19–7.05 (m, 12H), tube was then opened with care. The mixture was poured into
4.07 (d, J ¼ 10.5 Hz, 1H), 3.96 (d, J ¼ 10.5 Hz, 1H), 3.58–3.52 water, and the organic layer was separated. The aqueous layer
(m, 1H), 2.69 (dd, J ¼ 12.7, 7.5 Hz, 1H), 2.31 (s, 3H), 2.26–2.21 was extracted with dichloromethane. The organic layers were
(m, 1H), 2.00–1.94 (ddd, J ¼ 13.4, 7.6, 3.2 Hz, 1H), 1.22 (dd, combined, dried (MgSO4), and concentrated to give a crude
J ¼ 15.4, 10.8 Hz, 1H), 0.75 (t, J ¼ 7.4 Hz, 3H). 13C NMR (100 product which was puried by ash column chromatography to
61088 | RSC Adv., 2015, 5, 61081–61093
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