![](/CAS/GIF/675126-07-5.gif)
(1S,4R)-N-Desmethyl Sertraline Hydrochloride synthesis
- Product Name:(1S,4R)-N-Desmethyl Sertraline Hydrochloride
- CAS Number:675126-07-5
- Molecular formula:C16H16Cl3N
- Molecular Weight:0
![Formamide, N-[(1S,4R)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenyl]-](/CAS/20210305/GIF/674768-15-1.gif)
674768-15-1
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![(1S,4R)-N-Desmethyl Sertraline Hydrochloride](/CAS/GIF/675126-07-5.gif)
675126-07-5
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$155.00/1mg
Yield:> 99.8 % ee
Reaction Conditions:
with hydrogenchloride in methanol at 80; for 2 h;
Steps:
Synthesis of (1S,4R)-trans 4-(3, 4-dichlorophenyl) -1,2, 3, [4-TETRAHYDRO-1-] napthalenamine HCI
: (1S, [4R)] formamide (ca 300 mg) was dissolved in [MEOH] (5 mL) followed by addition of 6N HCl (6 mL). The reaction mixture was heated to [80°C] for 2 h. The reaction mixture was cooled to rt for 1 h and filtered to collect the solid. It was washed with acetone (3 mL) and dried to give the product (280 mg). Enantiomeric purity was determined to be >99.8% by HPLC analysis with a ChiralPak AD [10] [M,] 4.6 x 250 mm, Hexane/IPA/DEA (99: 1: 0.1), UV 220 [NM,] [(1R,] 4S)-isomer, 11.00 min. [(LS,] 4isomer 11.70 min [a] =-51° (C = 1, [MEOH).'H] NMR (CD30D) 8 1.86-1. 97 (m, 2H), 2.20-2. 42 (m, 2H), 4.30 (broad s, 1H), 4.67 (broad s, 1H), 4.87 (s, 3H), 6.95-6. 99 (m, 2H), 7.18 (s, 1H), 7.28-7. 50 (m, m, 4H). M+ 293
References:
WO2004/24669,2004,A1 Location in patent:Page 17