Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride, cas is 57060-88-5, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.
Step A N-(3,5-Dichlorobenzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester To a mixture of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester hydrochloride (200 mg, 0.878 mmol) in a 1:1 mixture of CH2Cl2 and THF (2.5 mL each) was added dropwise DIPEA (0.88 mmol, 113 mg) followed by 3,5-dichlorobenzenesulfonyl chloride (0.922 mmol, 227 mg), a second equivalent of DIPEA and 4-DMAP (0.176 mmol, 22 mg). The reaction mixture was stirred at rt overnight when TLC (4:1 hexane:ethyl acetate) indicated disappearance of all starting material. The volatiles were removed in vacuo and the residue was purified by flash column chromatography on silica gel eluted with a gradient of hexane and ethyl acetate to yield N-(3,5-dichlorobenzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester (282 mg, 80%) as a white foam, homogeneous by TLC (Rf=0.55, 4:1 hexane:ethyl acetate); 500 MHz 1H NMR (CDCl3): delta3.24 (m, 2H), 3.54 (s, 3H), 4.47 (d, J=15 Hz, 1H), 4.74 (d, J=15 Hz, 1H), 5.01 (dd, J=3.7, 6 Hz, 1H), 7.08-7.27 (m, 4H), 7.56 (t, J=1.8 Hz, 1H), 7.73 (d, J=1.9 Hz, 2H)., 57060-88-5
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Reference£º
Patent; Lin, Linus S.; Shah, Shrenik K.; Chang, Linda L.; Hagmann, William K.; Mumford, Richard A.; US2002/193399; (2002); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem