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Chemical Structure| 177202-62-9 Chemical Structure| 177202-62-9

Structure of 177202-62-9

Chemical Structure| 177202-62-9

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Product Details of [ 177202-62-9 ]

CAS No. :177202-62-9
Formula : C11H13NO2
M.W : 191.23
SMILES Code : COC(=O)C1CNC2=CC=CC=C2C1
English Name :Methyl 1,2,3,4-tetrahydroquinoline-3-carboxylate
MDL No. :MFCD14581740

Safety of [ 177202-62-9 ]

Application In Synthesis of [ 177202-62-9 ]

* 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.

  • Downstream synthetic route of [ 177202-62-9 ]

[ 177202-62-9 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 53951-84-1 ]
  • [ 177198-62-8 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; 1,4-dioxane; methanol; for 10h;pH 4;Inert atmosphere; To a solution of methyl ester 4 (7.68 g, 41 mmol) in dry tetrahydrofuran (150 mL) and methanol (70 mL) sodium cyanoborohydride (10.8 g, 172 mmol) was added under a nitrogen atmosphere. The pH was adjusted to 4, by the addition of 4 M hydrogen chloride in dioxane and kept at this value over the course of the reaction (10 h), by the addition of the same hydrogen chloride solution. The reaction progress was monitored by TLC (dichloromethane/acetone 9:1) until the starting material disappeared. The reaction mixture was cooled in an ice bath, after which water (200 mL) and a saturated sodium hydrogen carbonate aqueous solution (until neutral pH) were added. The organic solvents were removed at reduced pressure. The aqueous phase was extracted with ethyl acetate (3 x 200 mL). The collected organic phases were dried over sodium sulfate and after the usual work-up an oily residue (8.84 g) was obtained; the residue was purified by silica gel column chromatography by elution with hexane/ethyl acetate (9:1) to give pure 5 (6.88 g, 88%). The chemical and physical properties were in agreement with the reported ones.22
88% With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; 1,4-dioxane; methanol; for 10h;pH 4;Inert atmosphere; To a solution of methyl ester 4 (7.68 g, 41 mmol) in dry tetrahydrofuran (150 mL) and methanol (70 mL) sodium cyanoborohydride (10.8 g, 172 mmol) was added, under nitrogen atmosphere. The pH was adjusted at 4, by addition of 4M hydrogen chloride in dioxane and kept at this value, in the course of the reaction (10 h), by addition of the same hydrogen chloride solution. The reaction progress was monitored by TLC (dichloromethane/acetone 9:1) until the starting material disappearance. The reaction mixture was cooled in an ice bath, water (200 ml) and a saturated sodium hydrogen carbonate aqueous solution (until neutral pH) were added. Organic solvents were removed at reduced pressure. The aqueous phase was extracted with ethyl acetate (3*200 mL). The collected organic phases are dried over sodium sulfate and after usual work-up an oily residue (8.84 g) was obtained; the residue was purified by silica gel column chromatography: by elution with hexane/ethyl acetate (9:1) pure 5 was recovered (6.88 g, 88%). The chemical-physical properties are in agreement with the reported ones (Alatorre-Santamaria, S.; Gotor-Fernandez, V.; Gotor, V. Tetrahedron: Asymmetry 2010, 21, 2307-2313).
65% With hydrogenchloride; sodium cyanoborohydride; In 1,4-dioxane; methanol; at 25℃; for 12h; Compound 16-b (1.00 g, 5.34 mmol, 1.00 eq) was dissolved in methanol (12.50 mL), and NaBH3CN (1.68 g, 26.70 mmol, 5.00 eq) and HCl/dioxane (4 M, 8.00 mL, 5.99 eq) were added thereto. The reaction solution was stirred at 25C for 12 hours. After the reaction was completed, the reaction solution was added with 50 mL of water, and adjusted to pH of 7 with saturated sodium hydrogen carbonate solution. The above solution was extracted with ethyl acetate (100 mL 3 3). The organic phases were combined, washed successively with brine (100 mL) and water (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was subjected to column chromatography (petroleum ether : ethyl acetate = 1:0?1:1) to give the product of compound 16-c (800.00 mg, yield: 65%) as a yellow oil. LCMS m/z = 192.0 [M+H]+.
49% With hydrogenchloride; methanol; sodium cyanoborohydride; In 1,4-dioxane; at 20℃; for 16h;pH 4 - 5; To a solution of Intermediate- 11 (3g, 16.03mmol) in MeOH (100mL), sodium cyanoborohydride (5.04 g, 80 mmol) and then a small amount of bromocresol green (pH indicator) was added. 4M HCl solution in dioxane (5 mL X 3) in 30 min interval was added drop-wise into reaction mixture to make pH acidic (4 to 5), till reaction mixture maintained a yellow color then reaction mixture was stirred at RT for 16 h. Reaction was monitored by TLC/LCMS. After completion of reaction, the reaction mixture was quenched with sodium bicarbonate and extracted with ethyl acetate (20X3 mL). The combined organic layer was dried and concentrated under reduced pressure. The crude compound was purified by flash chromatography by using (20 % ethyl acetate in hexane) to get methyl 1,2,3,4-tetrahydroquinoline-3-carboxylate (1.5 g, yield 49%) as yellow color oily mass; m/z- 191.7
With borane pyridine; acetic acid; at 20℃; [00343] As depicted in Scheme 4-1, quinoline-3-carboxylic acid 3 was esterified with thionyl chloride in methanol to yield ester 4. Reduction of the pyridine ring of 4 with pyridine-borane complex in glacial acetic acid then delivered racemic THQ 5 whose methyl ester was saponified to yield ±-6. Alternatively, sulfonylation of ±-5 furnished compounds ±-7, which were also saponified with lithium hydroxide to afford the 3-carboxy target compounds ±-8. Further elaboration of the phenylsulfonyl group in ±-7c was accomplished by an SNAr reaction with 4- chloro-3,5-dimethylphenol followed by ester hydrolysis to afford compound ±-2, as shown in Scheme 4-2. In addition, the phenylsulfonyl moiety in ±-2 was replaced with a more flexible propylene group through a reductive amination-saponification sequence to yield ±-11.

  • 2
  • [ 53951-84-1 ]
  • [ 177198-62-8 ]
  • 5,6,7,8-tetrahydroquinoline-3-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With sodium hydrogencarbonate; trifluoroacetic acid;platinum (IV) oxide; In ethyl acetate; Preparation of 5,6,7,8-Tetrahydroquinoline-3-Carboxylic Acid Methyl Ester Representative procedure for small scale hydrogenation reactions. To a 2 or 3-neck, 100 ml round bottom flask containing a stir bar was added <strong>[53951-84-1]methyl quinoline-3-carboxylate</strong> (170 mg, 0.908 mmol) and platinum(IV) oxide (10.3 mg, 5 mol %). The flask was equipped with two outlets sealed with rubber septa and containing Teflon stopcocks. Trifluoroacetic acid (3.0 mL), which was purged with argon gas to remove oxygen, was added via a plastic syringe into the reaction flask under an atmosphere of nitrogen. The stirred reaction mixture was flushed and the flask filled with hydrogen gas via a needle from a balloon through one of the septa-sealed outlets. The Teflon stopcocks were closed and the reaction mixture was warmed to 60 C. and stirred for 5 hours. The progress of the reaction was monitored by GC and TLC. The reaction mixture was cooled to room temperature and aqueous saturated sodium bicarbonate solution was added until the mixture was neutral. The mixture was then extracted with CH2Cl2 (3*30 mL), dried (MgSO4), and the solvent was removed in vacuo. The crude material thus obtained was separated by flash chromatography (silica gel, 10% EtOAc in hexanes). The title compound was obtained as a yellowish liquid (121 mg, 70%) which displayed: 1H NMR (CDCl3, 300 MHz): delta 1.80-2.00 (m, 4H), 2.79-2.85 (m, 2H), 2.90-3.00 (m, 2H), 3.91 (s, 3H), 7.95 (s, 1H), 8.93 (s, 1H); 13C NMR (CDCl3): delta 22.8, 23.1, 28.9, 30.0, 33.1, 52.5, 123.7, 132.5, 138.0, 148.2, 162.6, 166.5; MS m/z: 192 (M+H+). 1,2,3,4-Tetrahydro<strong>[53951-84-1]quinoline-3-carboxylic acid methyl ester</strong> also was isolated (19 mg, 11%).
  • 3
  • [ 177202-62-9 ]
  • [ 79180-47-5 ]
YieldReaction ConditionsOperation in experiment
89% With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4h; Cooling with ice; 4.2.3. (RS)-3-(1'-Hydroxymethyl)-1,2,3,4-tetrahydroquinoline 3 To a suspension of lithium aluminum hydride (5.3 g, 140 mmol) in dry tetrahydrofuran (125 mL), cooled at 0-5 oC, ester 5 (6.68 g, 35 mmol) dissolved in tetrahydrofuran (125 mL) was added dropwise. The ice bath was then removed and the reaction mixture was kept at room temperature (4 h), with the reaction progress monitored by TLC (dichloromethane/acetone 9:1) until the starting material disappeared. To the reaction mixture, cooled at 0-5 oC, water (5.3 mL), 15% sodium hydroxide aqueous solution (5.3 mL), and water (16 mL) were sequentially added. The white precipitate was removed by suction through a Celite pad. The solvent was evaporated at reduced pressure and the recovered oily 3 (5.02 g,89%) was used in the next step without further purification. 1HNMR (CDCl3) δ 2.23 (m, 1H, H-3); 2.56 (dd, 1H, J = 16.17 and 8.40 Hz, H-4); 2.88 (dd, 1H, J = 16.17 and 5.18 Hz, H-4); 2.62-2.82 (m, 2H, exchange with D2O); 3.15 (dd, 1H, J = 8.09 and 11.14 Hz, H-2), 3.46 (ddd, 1H, J = 11.14, 3.51 and 1.52, H-2); 3.64 (dd, 1H, J = 11.14 and 7.62 Hz, H-10); 3.72 (dd, 1H, 11.14 and 5.95 Hz, H-10); 6.53 (d, 1H, J = 7.78 Hz, H-5); 6.67 (dd, 1H, J = 7.78 and 8.24 Hz, H-6); 6.97-7.05 (m, 2H, H-7 and H-8). 13C NMR (CDCl3) δ 29.56 (C-4); 34.91 (C-3), 44.03 (C-2); 65.23 (C-10); 114.16 (C-5); 117.36 (C-6); 120.21 (C-10); 126.84 (C-8); 129.82 (C-7); 144.48 (C-9). IR ν max 3380.86, 3238.16, 2918.32, 2864.52, 2837.38, 1602.37, 1582.56, 1494.88, 1471.35, 1368.95, 1323.05, 1293.83, 1266.81, 1071.36, 1022.97 cm-1; MS (ESI+) m/z 164.1 [M+1]+, 186.0 [M+Na]+.
89% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; 3 Preparation of (R,S)-3-(1'-hydroxy-methyl)-1,2,3,4-tetrahydroquinoline (compound 3) To a suspension of lithium aluminum hydride (5.3 g, 140 mmol) in dry tetrahydrofuran (125 mL), cooled at 0-5° C., ester 5 (6.68 g, 35 mmol), dissolved in tetrahydrofuran (125 mL) was added dropwise. The ice bath was then removed and the reaction mixture was kept at room temperature (4 h), monitoring the reaction progress by TLC (dichloromethane/acetone 9:1) until starting material disappearance. To the reaction mixture, cooled at 0-5° C., water (5.3 mL), 15% sodium hydroxide aqueous solution (5.3 mL) and water (16 mL) were sequentially added. The white precipitate was removed by suction through a Celite pad. The solvent was evaporated at reduced pressure and the recovered oily 3 (5.02 g, 89%) was used in the next step without any further purification. 1H NMR (CDCl3) δ 2.23 (m, 1H, H-3); 2.56 (dd, 1H, H-4); 2.88 (dd, H-4); 2.62-2.82 (m, 2H, exchange with D2O); 3.15 (dd, 1H, H-2), 3.46 (ddd, 1H, H-2); 3.64 (dd, 1H, H-1′); 3.72 (dd, 1H, H-1′); 6.53 (d, 1H, H-5); 6.67 (dd, 1H, H-6); 6.97-7.05 (m, 2H, H-7 and H-8). IR vmax 3380.86, 3238.16, 2918.32, 2864.52, 2837.38, 1602.37, 1582.56, 1494.88, 1471.35, 1368.95, 1323.05, 1293.83, 1266.81, 1071.36, 1022.97 cm-1 . MS (ESI+) m/z 164.1 [M+1]+, 186.0 [M+Na]+, 375 [2M+2Na]+.
With sodium hydroxide In diethyl ether 14.3 1-(5-Methyl-pyrazin-2-yl)-3-[5-methyl-2-(1,2,3,4-tetrahydro-quinolin-3-ylmethoxy)-phenyl]-urea Step 3: (1,2,3,4-Tetrahydro-quinolin-3-yl)-methanol. To a stirred solution of the 1,2,3,4-Tetrahydro-quinoline-3-carboxylic acid methyl ester (93 mg, 0.49 mmol) in 1.5 mL of Et2O at 0° C. under nitrogen was added LiA1H4 (1in Et2O) dropwise with vigorous gas evolution and a white precipitate formation. After 30 min., the reaction was carefully quenched with 15% NaOH (3 mL) and 3 mL of Et2O was added and the mixture stirred rapidly at RT for 15 min. The layers were separated and the aqueous layer extracted (1*10 mL) with Et2O. The organics were combined, dried (MgSO4), filtered and concentrated to the alcohol (64 mg, 80%). 1H-NMR (400 MHz, CDCl3) δ6.97 (m, 2H), 6.62 (dd, 1H), 6.47 (d, 1H), 3.66 (m, 1H), 3.58 (m, 1H), 3.40 (m, 1H), 3.08 (m, 1H), 2.82 (m, 1H), 2.53 (m, 1H), 2.18 (m, 1H).
  • 4
  • [ 177202-62-9 ]
  • [ 177198-71-9 ]
YieldReaction ConditionsOperation in experiment
With N-butylamine 25 5(S)-Amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-butylaminocarbonyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide The amine component employed as the starting material is prepared, for example as follows: A mixture of 500 mg of 3(R,S)-methoxycarbonyl-1,2,3,4-tetrahydroquinoline (Example 1r) and 1 ml of n-butylamine is stirred at 60° C. for 1 h. Purification of the crude product by means of FC over 50 g of silica gel (mobile phase Z) gives 3(R,S)-butylaminocarbonyl-1,2,3,4-tetrahydroquinoline: Rf (Z)=0.21.
  • 5
  • [ 177202-62-9 ]
  • [ 177202-69-6 ]
YieldReaction ConditionsOperation in experiment
In <i>N</i>-methyl-acetamide; methylamine 69 5(S)-Amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-methylaminocarbonyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide The amine component employed is prepared starting from 1.2 g of 3(R,S)-methoxycarbonyl-1,2,3,4-tetrahydroquinoline, with reaction in 10 ml of a 3N methylamine solution in dimethylformamide at 50° C. for 30 h. Purification of the crude product, after concentration of the reaction mixture, by means of FC over silica gel (mobile phase N) gives 3(R,S)-methylaminocarbonyl-1,2,3,4-tetrahydroquinoline as a white solid: Rf (N)=0.25.
  • 6
  • [ 177198-65-1 ]
  • [ 177202-62-9 ]
YieldReaction ConditionsOperation in experiment
In methanol; palladium 1.r r r 3(R,S)-Methoxycarbonyl-1,2,3,4-tetrahydroquinoline is obtained by hydrogenation of 495 mg of N-benzyloxycarbonyl-3(R,S)-methoxycarbonyl-1,2,3,4-tetrahydroquinoline in the presence of 100 mg of palladium-on-charcoal (10% of Pd) in 20 ml of methanol at room temperature under normal pressure for 4 h. The reaction mixture is filtered over Hyflo and concentrated. The title compound is obtained as a pure oil: Rf (D)=0.28; Rt (II)=3.5 min; FAB-MS: (M)+ =191.
  • 7
  • [ 109-21-7 ]
  • [ 177202-62-9 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With Rhizomucor miehei lipase In tetrahydrofuran at 30℃; for 34h; Inert atmosphere; Resolution of racemate; Enzymatic reaction; enantioselective reaction;
  • 8
  • [ 177202-62-9 ]
  • [ CAS Unavailable ]
  • [ 1256479-01-2 ]
YieldReaction ConditionsOperation in experiment
70% With thionyl chloride at 120℃; Cooling with ice;
  • 9
  • [ 177202-62-9 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With Rhizomucor miehei lipase In tetrahydrofuran at 30℃; for 34h; Inert atmosphere; Resolution of racemate; Enzymatic reaction; enantioselective reaction;
  • 10
  • [ 177202-62-9 ]
  • [ 278789-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C
  • 11
  • [ 177202-62-9 ]
  • [ 1462979-37-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pseudomonas fluorescens lipase / toluene / 20 °C / Enzymatic reaction
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pseudomonas fluorescens lipase / toluene / 66 h / 20 °C / Enzymatic reaction
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pyridine / 20 °C
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pyridine / 20 °C

  • 12
  • [ 177202-62-9 ]
  • [ 1462979-41-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pseudomonas fluorescens lipase / toluene / 20 °C / Enzymatic reaction
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: vinyl acetate; pseudomonas fluorescens lipase / toluene / Enzymatic reaction
  • 13
  • [ 177202-62-9 ]
  • [ 1462979-42-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pseudomonas fluorescens lipase / toluene / 20 °C / Enzymatic reaction 4: sodium hydroxide; pseudomonas fluorescens lipase / aq. phosphate buffer / 5 h / pH 7 / Enzymatic reaction
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pseudomonas fluorescens lipase / toluene / 66 h / 20 °C / Enzymatic reaction 4: sodium hydroxide; pseudomonas fluorescens lipase / aq. phosphate buffer / 5 h / pH 7 / Enzymatic reaction
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pyridine / 20 °C 4: sodium hydroxide; pseudomonas fluorescens lipase / aq. phosphate buffer / 5 h / pH 7 / Enzymatic reaction
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pyridine / 20 °C 4: pseudomonas fluorescens lipase / aq. phosphate buffer / 5 h / pH 7 / Enzymatic reaction

  • 14
  • [ 177202-62-9 ]
  • [ 1462979-36-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pseudomonas fluorescens lipase / toluene / 20 °C / Enzymatic reaction 4: pyridine / 4 h / 20 °C / Cooling with ice 5: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C 6: trifluoroacetic acid / dichloromethane / 20 °C
Multi-step reaction with 6 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Cooling with ice 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pseudomonas fluorescens lipase / toluene / 66 h / 20 °C / Enzymatic reaction 4: pyridine / 4 h / 20 °C / Cooling with ice 5: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C 6: trifluoroacetic acid / dichloromethane / 20 °C
Multi-step reaction with 6 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: pseudomonas fluorescens lipase / toluene / Enzymatic reaction 4: pyridine / 20 °C / Cooling with ice 5: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C 6: trifluoroacetic acid / dichloromethane / 20 °C
Multi-step reaction with 6 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C 2: sodium hydroxide / 1,4-dioxane; water / 24 h / 20 °C 3: vinyl acetate; pseudomonas fluorescens lipase / toluene / Enzymatic reaction 4: pyridine / 20 °C / Cooling with ice 5: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C 6: trifluoroacetic acid / dichloromethane / 20 °C

 

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