(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
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
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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
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September 2014 to celebrate the 15th anniversary of Professor Lv Wei from previous teaching students gathering
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