K.-K. Wang, Y.-L. Li, G.-Y. Ma, M.-H. Yi, and B.-K. Zhu
Vol 000
1-Benzyl-3-(phenylsulfonyl)pyrrolidine (6a).
27.7 mg,
E.; Townson, K.; Wheeldon, A.; Boyce, S.; Collinson, N.; Rupniak, N.;
DeVita, R. J. Bioorg Med Chem Lett 2010, 20, 5925; (b) Okada, M.;
Sugita, T.; Abe, I. Beilstein J Org Chem 2017, 13, 338; (c) Stockdale,
T. P.; Williams, C. M. Chem Soc Rev 2015, 44, 7737.
[2] (a) Naesborg, L.; Tur, F.; Meazza, M.; Blom, J.; Halskov, K.
S.; Jorgensen, K. A. Chem A Eur J 2017, 23, 268; (b) Qi, J.; Duan,
X.-Y.; Cao, L.-L.; Wang, W.-Y. Asian J Org Chem 2015, 4, 1254.
[3] Bolognesi, M. L.; Bartolini, M.; Cavalli, A.; Andrisano, V.;
Rosini, M.; Minarini, A.; Melchiorre, C. J Med Chem 2004, 47, 5945.
[4] Cox, J. M.; Chu, H. D.; Kuethe, J. T.; Gao, Y. D.; Scapin, G.;
Eiermann, G.; He, H. B.; Li, X. H.; Lyons, K. A.; Metzger, J.; Petrov, A.;
Wu, J. K.; Xu, S. Y.; Sinha-Roy, R.; Weber, A. E.; Biftu, T. Bioorg Med
Chem Lett 2016, 26, 2622.
1
92% yield, pale yellow oil; H-NMR (400 MHz, CDCl3)
δ 7.82 (d, J = 7.2 Hz, 2H), 7.58 (t, J = 7.6 Hz, 1H), 7.49
(t, J = 8.0 Hz, 2H), 7.24–7.21 (m, 2H), 7.19–7.15 (m,
3H), 3.71–3.64 (m, 1H), 3.53 (q, J = 12.8 Hz, 2H), 2.80
(d, J = 7.6 Hz, 2H), 2.66–2.61 (m, 1H), 2.49 (dd,
J = 16.0, 7.6 Hz, 1H), 2. 27–2.19 (m, 1H), 2.08–1.98 (m,
1H). 13C-NMR (100 MHz, CDCl3) δ 138.4, 138.3, 133.8,
129.3, 128.7, 128.6, 128.4, 127.2, 62.6, 59.6, 53.8, 53.4,
25.9. ESI-HRMS: calcd for C17H19NO2S + H+ 302.1209,
[5] (a) Picciche, M.; Pinto, A.; Griera, R.; Bosch, J.; Amat, M. Org
Lett 2017, 19, 6654; (b) Xiao, J.; Xu, F. X.; Lu, Y. P.; Loh, T. P. Org Lett
2010, 12, 1220.
found 302.1206.
1-Benzyl-3-((4-chlorophenyl)sulfonyl)pyrrolidine (6b).
31.2 mg, 93% yield, pale yellow oil; 1H-NMR
(400 MHz, CDCl3) δ 7.81 (d, J = 8.4 Hz, 2H), 7.52 (d,
J = 8.8 Hz, 2H), 7.32–7.25 (m, 3H), 7.20 (d, J = 7.2 Hz,
2H), 3.76–3.68 (m, 1H), 3.58 (q, J = 13.2 Hz, 2H), 2.89–
2.81 (m, 2H), 2.70–2.64 (m, 1H), 2.58 (dd, J = 16.0,
7.6 Hz, 1H), 2.31–2.22 (m, 1H), 2.17–2.07 (m, 1H). 13C-
NMR (100 MHz, CDCl3) δ 140.5, 138.0, 136.7, 130.1,
129.5, 128.5, 128.3, 127.2, 62.7, 59.4, 53.7, 53.2, 25.8.
ESI-HRMS: calcd for C17H18ClNO2S + H+ 336.0820,
found 336.0815.
[6] For selected reviews of 1,3-dipolar cycloaddition reaction,
see:(a) Dondas, H. A.; de Gracia Retamosa, M.; Sansano, J. M. Synthe-
sis-Stuttgart 2017, 49, 2819; (b) Bdiri, B.; Zhao, B.-J.; Zhou, Z.-M.
Tetrahedron-Asymmetry 2017, 28, 876; (c) Singh, M. S.; Chowdhury,
S.; Koley, S. Tetrahedron 2016, 72, 1603; (d) Ryan, J. H. ARKIVOC
2015, 2015, 160; (e) Hashimoto, T.; Maruoka, K. Chem Rev 2015,
115, 5366; (f) Narayan, R.; Potowski, M.; Jia, Z.-J.; Antonchick, A.
P.; Wadmann, H. Acc Chem Res 2014, 47, 1296; (g) Adrio, J.;
Carretero, J. C. Chem Commun 2014, 50, 12434; (h) Coldham, I.;
Hufton, R. Chem Rev 2005, 105, 2765; (i) De, N.; Yoo, E. J. ACS
Catal 2018, 8, 48; (j) Li, J.-L.; Dai, Q.-S.; Yang, K.-C.; Liu, Y.; Zhang,
X.; Leng, H.-J.; Peng, C.; Huang, W.; Li, Q.-Z. Org Lett 2018, 20,
7628; (k) Li, Q.; Zhou, L.; Shen, X.-D.; Yang, K.-C.; Zhang, X.;
Dai, Q.-S.; Leng, H.-J.; Li, Q.-Z.; Li, J.-L. Angew Chem Int Ed
2018, 57, 1913.
General procedure synthetic transformation of product
4a.
To a solution of compound 4a (0.5 mmol,
[7] For selected examples, see: (a) McAlpine, I.; Tran-Dube, M.;
Wang, F.; Scales, S.; Matthews, J.; Collins, M. R.; Nair, S. K.; Nguyen,
M.; Bian, J.; Alsina, L. M.; Sun, J.; Zhong, J.; Warmus, J. S.; O’Neill,
B. T. J Org Chem 2015, 80, 7266; (b) Lee, S.; Diab, S.; Queval, P.;
Sebban, M.; Chataigner, I.; Piettre, S. R. Chem A Eur J 2013, 19, 7181;
(c) Moshkin, V. S.; Sosnovskikh, V. Y.; Slepukhin, P. A.;
Roeschenthaler, G.-V. Mendeleev Commun 2012, 22, 29; (d)
Starosotnikov, A. M.; Bastrakov, M. A.; Pechenkin, S. Y.; Leontieva,
M. A.; Kachala, V. V.; Shevelev, S. A. J Heterocyclic Chem 2011, 48,
824; (e) Davoren, J. E.; Gray, D. L.; Harris, A. R.; Nason, D. M.; Xu,
W. Synlett 2010, 2010, 2490; (f) Roy, S.; Kishbaugh, T. L. S.; Jasinski,
J. P.; Gribble, G. W. Tetrahedron Lett 2007, 48, 1313; (g) Moshkin, V.
S.; Buev, E. M.; Sosnovskikh, V. Y. Tetrahedron Lett 2015, 56, 5278;
(h) Buev, E. M.; Moshkin, V. S.; Sosnovskikh, V. Y. Org Lett 2016,
18, 1764; (i) Ryan, J. H.; Spiccia, N.; Wong, L. S. M.; Holmes, A. B. Aust
J Chem 2007, 60, 898; (j) D’Souza, A. M.; Spiccia, N.; Basutto, J.; Jokisz,
P.; Wong, L. S. M.; Meyer, A. G.; Holmes, A. B.; White, J. M.; Ryan, J.
H. Org Lett 2011, 13, 486; (k) Santos, H.; Distiller, A.; D’Souza, A. M.;
Arnoux, Q.; White, J. M.; Meyer, A. G.; Ryan, J. H., Org Chem Front
2015, 2, 705; (l) Li, S.-n.; Yu, B.; Liu, J.; Li, H.-l.; Na, R. Synlett 2016,
27, 282; (m) Bastrakov, M. A.; Starosotnikov, A. M.; Pechenkin, S. Y.;
Kachala, V. V.; Glukhov, I. V.; Shevelev, S. A. J Heterocyclic Chem
2010, 47, 893; (n) Buev, E. M.; Moshkin, V. S.; Sosnovskikh, V. Y. J
Org Chem 2017, 82, 12827.
149.5 mg) in MeOH (5 mL) was added the Pd/C (5% wt
Pd on carbon, 15 mg, 10 wt%), followed by degassing
with H2 for three times at room temperature, and the
resultant mixture was then stirred under a balloon
pressure of H2 for 10 h until the reaction was completed
as monitored by thin-layer chromatography analysis.
Then, the reaction mixture was filtrated off through a
celite pad. The filtrate was concentrated under vacuum,
and the residue was purified by a flash column
chromatography on silica gel (CH2Cl2/MeOH = 20:1) to
give the product 7 (96.1 mg, 92% yield) as a colorless oil.
(3aR,8bR)-2,3,3a,8b-tetrahydro-1H-benzo[4,5]thieno[2,3-c]
pyrrole 4,4-dioxide (7).
1H-NMR (400 MHz, CDCl3) δ
7.65–7.59 (m, 2H), 7.46 (t, J = 7.6 Hz, 1H), 7.39 (d,
J = 8.0 Hz, 1H), 4.22–4.17 (m, 1H), 3.89–3.83 (m, 2H),
3.24–3.17 (m, 2H), 3.09 (dd, J = 13.6, 7.6 Hz, 1H), 1.82
(s, 1H). 13C-NMR (100 MHz, CDCl3) δ 139.8, 139.2,
134.3, 129.3, 126.8, 121.1, 64.5, 55.8, 50.0, 47.4. ESI-
HRMS: calcd for C10H11NO2S + H+ 210.0583, found
210.0584.
[8] (a) Jereb, M. Green Chem 2012, 14, 3047; (b) Brant, M. G.;
Wulff, J. E. Synthesis 2016, 48, 1; (c) Li, F.; Chen, J.; Hou, Y.; Li, Y.;
Wu, X.-Y.; Tong, X. Org Lett 2015, 17, 5376.
[9] (a) Harada, M.; Kato, S.; Haraguchi, R.; Fukuzawa, S.-i. Chem
A Eur J 2018, 24, 2580; (b) Deng, H.; He, F.-S.; Li, C.-S.; Yang, W.-L.;
Deng, W.-P. Org Chem Front 2017, 4, 2343; (c) Lakshmi, N. V.;
Thirumurugan, P.; Jayakumar, C.; Perumal, P. T. Synlett 2010, 6, 955;
(d) Asian Journal of Organic ChemistryMalatesti, N.; Boa, A. N.; Clark,
S.; Westwood, R. Tetrahedron Lett 2006, 47, 5139.
[10] CCDC 1851340 contains the supplementary crystallographic
data for compound 4a. The data can be obtained free of charge from
getstructures.
Acknowledgments. We are grateful to the National Natural
Science Foundation of China (21801214) and the Higher Educa-
tion Institution Key Research Project Plan of Henan Province of
China (18A150014) for support of this research.
REFERENCES AND NOTES
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet