(S)-N-(2-(6-Methoxy-2,3-dihydro-1H-inden-1-yl)ethyl)propionamide

(S)-N-(2-(6-Methoxy-2,3-dihydro-1H-inden-1-yl)ethyl)propionamide

1: [a]D20 10.0 (c, 0.20, EtOH); mp 76–77 deg C;

1H NMR (500 MHz, CDCl3): d1.15 (t, 3H, J = 7.5 Hz), 1.60 (m, 1H), 1.70 (m, 1H), 2.02 (m, 1H), 2.19 (q, 2H, J = 7.5 Hz), 2.32 (m, 1H), 2.76 (m, 1H), 2.85 (m, 1H), 3.11 (m,
1H), 3.41 (m, 2H), 3.79 (s, 3H), 5.48 (s, 1H), 6.71 (dd, 1H, J = 2.0 Hz, 8.5 Hz), 6.75 (s, 1H), 7.11 (d, 1H, J = 8.0 Hz).

13C NMR (100 MHz,DMSO–d6): d 173.7, 158.7, 148.1, 135.8, 124.9, 112.3, 109.2, 55.5, 42.7, 37.9, 34.8, 32.5, 30.6, 29.8, 9.9. EI-MS: 247 ([M]+); HR-MS 247.1572
([M]+, C15H21NO2; Calcd. 247.1571).

The enantiomeric excess of (S)-1 was determined by HPLC as >99.9% [column, CHIRALPAK AS-H
(4.6 mm 250 mm), room temperature; eluent, hexane-2-propanol-trifluoroacetic acid (90:10:0.1); flow rate, 1.0 mL/min; detect, 290 nm; tR
of (S)-1, 30.7 min; tR of (R)-1 (enantiomer of (S)-1), 37.1 min].

S.B. Yu et al. / Chinese Chemical Letters 22 (2011) 264–267
: wlu@chem.ecnu.edu.cn (W. Lu).
Synthesis of the key intermediate of ramelteon
Shan Bao Yu a, Hao Min Liu a, Yu Luo a, Wei Lu b,


*a Department of Chemistry, East China Normal University, Shanghai 200062, China

b Institute of Drug Discovery and Development, East China Normal University, Shanghai 200062, China

http://sat.ecnu.edu.cn/Uploadnews/20120213113859628.pdf
and

https://www.heterocycles.jp/newlibrary/downloads/PDF/22186/85/1

Yu Luo

Associate Professor

Department of Chemistry

Institute of Technology Department of Chemistry

Tel: 021-54345462

Office Hours: Monday to Saturday 9: 00-19: 00

Fax:

Home URL:

Office Location: Minhang Chemistry Building 535

E-mail: yluo@chem.ecnu.edu.cn

Mailing address: 500 Dongchuan Road, East China Normal University Minhang Campus Chemistry Building 535

Research

(1) small molecule medicinal chemistry research. Including anticancer drugs, anti-hepatitis drugs and hypoglycemic drug design, synthesis and pharmacological properties of (2) study of drug synthesis and fine chemicals. Includes a plurality of anticancer drugs, vitamin D drugs, natural phospholipids, as well as new anti-HIV drugs condensing agent, amino acid synthesis Studies link like fine chemicals (3) research initiative targeted drug delivery technology based on liposomes, microspheres, vesicles, etc.

Affiliations

Academic Achievements

Recently published research papers  1. Chen, TJ; Luo Y*; Hu, YH; Yang, B; Lu W, European Journal of Medicinal Chemistry, 2013, 64, 613-620 2. Zhang, X; Zhang, J; Tong, LJ; Luo, Y; Su, MB; Zhang, Y; Li, J; Lu, W*; Chen, Y*, Bioorganic & Medicinal Chemistry, 2013, 21, 3240-3244. 3. Luo, P; Luo, Y; Huang, J; Lu, W; Luo, DJ; Yu, JH*, Liu, SY, Colloids and Surfaces B: Biointerfaces, 2013, 109, 167-175.  4. Mei, TW; Luo, Y*, Feng, XJ; Lu, W*; Yang, B,  Tetrahedron, 2013, 69, 2927 – 2932 5. Wu, QE; Du, F; Luo, Y; Lu, W; Huang, J; Yu, JH*; Liu, SY*, Colloids and Surfaces B: Biointerfaces, 2013, 105, 294-302.  6. Yong, DW; Luo, Y; Du, F; Huang, J; Lu, W; Dai, ZY; Yu, JH*; Liu, SY*, 2013, 105, 31-36. 7. Chen, TJ; Huang, QQ; Luo, Y*, Hu, YH*, Lu, W, Tetrahedron Letters, 2013, 54, 1401-1404. 8. Luo,Y; Yu, SB; T, LJ; H, QQ; Lu, W; Chen, Y. European Journal of Medicinal Chemistry, 2012, 54, 281-286. 9. Feng, XJ; Mei YH; Luo, Y*; Lu W, Monatshefte fur Chemie - Chemical Monthly, 2012, 143 , 161-164 10. Yu, SB; Huang, QQ; Luo, Y*; Lu, W*, Journal of Organic Chemistry 2012, 77, 713-717. 11. Song, Y; Yuan, W; Luo, Y*; Lu, W Chinese Chemical Letters 2012, 23, 154-156. 12. Zhang, LJ; Luo, Y; Yu, SB; Lu, W*,  Journal of Heterocyclic Chemistry, 2012, 49, 1254-1256 13. Luo, Y; Xiao, F; Qian, SJ; He, QJ; Lu, W*; Yang, B* Synthesis and Evaluation of Novel 5-a, ß-unsaturated sulfonyl-indolin-2-ones as Potent Cytotoxic Agents,MedChemCommun, 2011, 2, 1054 - 1057 14. Luo, Y; Liu, HM; Su, MB; Sheng, L; Zhou, YB; Li, J*; Lu, W* Synthesis and Biological Evaluation of Piper Amide Analogues as HDAC Inhibitors, Bioorganic & Medicinal Chemistry Letters, 2011, 21, 4844-4866 15. Zhang, LJ; Xia, WP; Wang, B; Luo, Y*; Lu, W*, Convenient Synthesis of Sorafenib and ItsDerivatives, Synthetic Communications, 2011, 41, 3140-3146 16. Luo, Y; Xiao, F; Qian, SJ; Lu, W*, Yang, B, Synthesis and in vitro cytotoxic evaluation of some thiazolylbenzimidazole derivatives, European Journal of Medicinal Chemistry,2011, 46, 417-422. 17. Luo, Y; Yao, JP; Yang, L; Feng, CL; Tang, W; Wang, GF; Zuo, JP*; Lu, W*, Synthesis and Anti-Hepatitis B Virus Activity of a Novel Class of Thiazolylbenzimidazole Derivatives, Arch. Pharm. Chem. Life Sci. 2011, 2, 78–83 18. Yu, SB; Liu, HM; Luo, Y; Lu, W*, Synthesis of the key intermediate of ramelteon, Chinese Chemical Letters, 2011, 22，264–267 19. Luo, Y; Yao, JP; Yang, L; Feng, CL; Tang, W; Wang, GF; Zuo, JP*; Lu, W*, Design and synthesis of novel benzimidazole derivatives as inhibitors, Bioorganic & Medicinal Chemistry, 2010, 18, 5048-5055. 20. Liu, HY; Xia, WP; Luo, Y; Lu, W*, A novel synthesis of imatinib and its intermediates, Monatshefte fur Chemie - Chemical Monthly, 2010, 141, 907-911. 21. Yu, SB; Luo, Y; Liu, HY; Liu, HM; Lu, W*, Synthesis of the DE synthon of racemic camptothecin, Monatshefte fur Chemie - Chemical Monthly, 2010, 141, 245-249. 22. Wang, B; Zhang, LJ; Fu, KY; Luo, Y*； Lu, W; Tang, J, An Efficient Synthesis of 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one, Organic Preparations and Procedures International, 2009, 41, 309-314. Granted patent ZL201010137564.1; Synthesis method phosphatidylethanolamine ZL200910049896.1; multi-substituted pyridone compound synthesis ZL200910054400.X; key intermediate in the synthesis method for the preparation of camptothecin compounds ZL200710066688.3; a water-soluble derivative of camptothecin and its preparation method and application ZL200810034511.X; (2- cyano - isopropyl) - Preparation of 3,5-toluene ZL200910114955.9; one kind morpholine-carboxylic acid amides of N, N- dimethyl-4- do ZL200810042729.X; Synthesis of 1,2,6,7-tetrahydro -8H- indeno [5,4-b] furan-8-one Method The research project National Drug Discovery major projects a sub-topics,Shanghai Natural Science Foundation 1, the Ministry of Education funds a young teacher, the State Key Laboratory of Drug Research Fund 1, business cooperation projects 5

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