Structure of 91640-73-2
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CAS No. : | 91640-73-2 |
Formula : | C12H15NO2 |
M.W : | 205.25 |
SMILES Code : | O=C(OC)CC1NCCC2=C1C=CC=C2 |
MDL No. : | MFCD12827811 |
InChI Key : | ZYKBDGYQTKXXTM-UHFFFAOYSA-N |
Pubchem ID : | 45588337 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | 2-(1,2,3,4-Tetrahydroisoquinolin-1-yl)acetic acid methyl ester; 2-(1,2,3,4-Tetrahydroisoquinolin-1-yl)acetic acid (7.90 g, 41.3 mmol) was dissolved in methanol (200 ml), and H2SO4 (4.4 ml, 82.6 mmol) was added under a nitrogen atmosphere. The reaction solution was heated under reflux and, when the reaction was complete, was stirred overnight at room temperature. The methanol was removed in vacuo and the resulting residue was taken up in ethyl acetate (200 ml). The solution was washed with saturated NaHCO3 solution (150 ml), dried (sodium sulfate) and concentrated.Yield: 7.50 g (88%) | |
85% | H2SO4 (6.4 ml, 120 mmol) was added to a solution of the acid (11.50 g, 60.1 mmol) in MeOH (250 ml) under an N2 atmosphere and the mixture was stirred under reflux for 5 h. The reaction mixture was cooled to RT overnight. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (250 ml). The organic phase was washed with aqueous saturated NaHCO3 solution (250 ml). The organic phase was separated off, dried over Na2SO4 and filtered off and the solvent was removed in vacuo. Yield: 10.53 g, 85%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at 0℃; for 0.75h; | To a 0 C. solution of material from Step 1 (50.5 g, 240.0 mmol) in 250 mL dry THF was added di-tert-butyl dicarbonate (59.3 g, 270.0 mmol) in 50 mL dropwise. After siring for about 45 minutes, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate and brine, and then dried (Na2SO4) and concentrated in vacuo. Chromatography of the residue afforded both enantiomers of the title compound. EIS-MS: 306 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium tris(acetoxy)borohydride; In 1,1-dichloroethane; water; at 20℃; for 16.0h; | To a solution of material from Step 1 (6.71 g, 32.0 mmol) in 175 mL of dichloroethane was added 37% aqueous formaldehyde (22.6 mL, 300 mmol). After about 10 minute, sodium triacetoxyborohydride (31.2 g, 147.0 mmol) was added in 2 to 3 g portions with some cooling to maintain ambient temperature. The mixture was stirred for about 16 hours and DCM and water was added. The mixture was adjusted to pH 9-10 with 5N sodium hydroxide. The organic layer was separated, washed with brine, and then dried (Na2SO4) and concentrated in vacuo. Chromatography (silica gel, 5%(2N ammonia in methanol)/DCM) of the residue afforded about 6.9 g (96%) of the title compound. EIS-MS: 220 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogenchloride; methanol; | To a solution 100.4 g (52 mol) of Boc-tetrahydo isoquinoline-1-acetic (100.4 g, 520.0 mmol) in 200 mL methanol was added 400 mL of 2.3 M HCl in methanol. The mixture was stirred overnight and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate, brine, and then dried (Na2SO4) and concentrated in vacuo to afford about 109.5 g (100%) of the title compound. EIS-MS: 206 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrogenchloride; In 1,4-dioxane; at 20℃; for 1.0h; | The material from Preparation of 13C Step 2 (9.98 g, 32.7 mmol) was mixed with 500 mL cold 4M HCl/dioxane and stirred at r.t. for about an hour. The mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and then washed with saturated sodium bicarbonate and brine. The organic portion was dried (Na2SO4), filtered and concentrated in vacuo to afford about 6.9 g (100%) of the title compound. EIS-MS: 206 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 0℃; for 3.0h; | Methyl 2-(2-(3,4-dichlorophenylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)-acetate; <strong>[91640-73-2]2-(1,2,3,4-Tetrahydroisoquinolin-1-yl)acetic acid methyl ester</strong> (7.49 g, 36.5 mmol) was dissolved in DCM (200 ml), and triethylamine (11.7 ml, 83 mmol) was added thereto. The reaction solution was cooled to 0 C., and a solution of 3,4-dichlorobenzenesulfonyl chloride (8.14 g, 33.2 mmol) in DCM (100 ml) was added dropwise. After 3 h, 0.5 M HCl (100 ml) was added. After phase separation, the organic phase was washed with water, dried (sodium sulfate) and concentrated. Purification was carried out by column chromatography on silica gel (heptane/ethyl acetate 4:1).Yield: 14.84 g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triethylamine; In dichloromethane; at 0 - 20℃; | 2-(2-(4-Methoxyphenylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic acid S15; Methyl 2-(2-(4-methoxyphenylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate; <strong>[91640-73-2]2-(1,2,3,4-Tetrahydroisoquinolin-1-yl)acetic acid methyl ester</strong> (9.55 g, 46.5 mmol) was dissolved in DCM (150 ml), and triethylamine (14.9 ml, 106 mmol) was added thereto. The reaction mixture was cooled to 0 C., and a solution of methoxybenzenesulfonyl chloride (8.74 g, 42.3 mmol) in DCM (100 ml) was added dropwise thereto. The reaction mixture was stirred overnight at room temperature. For working up, 100 ml of a 0.5 M HCl solution were added and then the phases were separated. The organic phase was first washed with water and then dried over sodium sulfate. The crude product was purified by column chromatography on silica gel (mobile phase: DCM).Yield: 15.22 g (96%) |
96% | With triethylamine; In dichloromethane; at 0 - 20℃; | Et3N (14.9 ml, 106 mmol) was added to a solution of the ester (9.55 g, 46.5 mmol) in CH2Cl2 (150 ml). The reaction mixture was cooled to 0 C. and a solution of the sulfonyl halide (42 mmol) in CH2Cl2 (100 ml) was added dropwise. After stirring at RT overnight, 0.5 M HCl (100 ml) was added and the organic phase was separated off and washed with water. After drying over Na2SO4 and filtration, the solvent was removed in vacuo. The product was purified via column chromatography (silica, CH2Cl2). Yield: 15.22 g 96%. |
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