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[ CAS No. 35613-44-6 ]

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Chemical Structure| 35613-44-6
Chemical Structure| 35613-44-6
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CAS No. :35613-44-6 MDL No. :MFCD04973395
Formula : C9H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :165.19 g/mol Pubchem ID :5743389
Synonyms :

Safety of [ 35613-44-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 35613-44-6 ]

  • Upstream synthesis route of [ 35613-44-6 ]
  • Downstream synthetic route of [ 35613-44-6 ]

[ 35613-44-6 ] Synthesis Path-Upstream   1~8

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  • [ 35613-44-6 ]
  • [ 61-70-1 ]
Reference: [1] Patent: US2015/197511, 2015, A1,
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  • [ 30095-98-8 ]
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YieldReaction ConditionsOperation in experiment
97% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; Preparation of methyl 2-(2-aminophenyl)acetate (Compound 6-1) [00231j A mixture of Compound 1-2 (9.75 g, 50 mmol), 10percent palladiumlactivecarbon catalyst (dry, 530 mg, 5 mmol) in methanol (100 mL) was stirred under hydrogen atmosphere at room temperature for overnight. The reaction mixture was filtered to remove palladiumlactive carbon catalyst and the filtrate was concentrated to give Compound 6-1 (8.02 g, yield: 97percent) as a pale yellow oil. MS (ES): mlz:166[M+H]. ‘H NMR (400 MHz, DMSO-d6) ö: 6.94 (m, 2H), 6.64 (d, 1H, J 8.0 Hz),6.51 (m, 1H), 4.88 (s, 2H), 3.59 (s, 3H), 3.52 (s, 2H).
97% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; Preparation of methyl 2-(2-aminophenyl)acetate (Compound 11-3)[00269j A mixture of methyl 2-(2-nitrophenyl)acetate (Compound 11-2, 9.75 g, 50 mmol), 10percent palladiumlactive carbon catalyst (dry, 530 mg, 5 mmol) in methanol (100 mL) was stirred under H2 (1 atm.) at room temperature overnight. The reaction mixture was filtered to remove palladiumlactive carbon catalyst and the filtrate was concentrated to give the desired product methyl 2-(2-aminophenyl)acetate (Compound 11-3, 8.02 g, yield: 97percent) as a pale yellow oil. MS (ESI): mlz: 166[M+H]. ‘H NMR (400 MHz, DMSO-d6) ö: 6.94 (m, 2H), 6.64 (d, 1H, J= 8.0 Hz), 6.51 (m, 1H), 4.88 (s, 2H), 3.59 (s, 3H), 3.52 (s, 2H).
67% With hydrogen In ethyl acetate at 20℃; for 2 h; The 2-nitrophenyl acid methyl ester (1 g, 5.13 mmol) was dissolved in 20 mL of EA and 0.3 g of Pd/C 10percent was suspended into the solution, the reaction mixture was under hydrogen atmosphere at room temperature. After 2h the reaction was completed by TLC analysis (DCM: EA 60; 40) the Pd/C 10percent was removed by filtration and the solvent by reduced pressure; to yield a colorless oil 0.67 g (67percent).
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 5, p. 691 - 701
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 14, p. 1889 - 1893
[3] Patent: WO2014/106238, 2014, A1, . Location in patent: Paragraph 00231
[4] Patent: WO2014/106238, 2014, A1, . Location in patent: Paragraph 00269; 00397
[5] Patent: WO2009/3970, 2009, A1, . Location in patent: Page/Page column 42-43
[6] Journal of the American Chemical Society, 1937, vol. 59, p. 2348,2350
[7] Journal of the American Chemical Society, 1983, vol. 105, # 1, p. 74 - 79
[8] Journal of Organic Chemistry, 1995, vol. 60, # 8, p. 2326 - 2327
[9] Tetrahedron, 1997, vol. 53, # 48, p. 16521 - 16532
[10] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 17, p. 2891 - 2893
[11] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 14, p. 4396 - 4401
[12] Patent: US2005/101587, 2005, A9,
[13] Patent: WO2003/82841, 2003, A1, . Location in patent: Page/Page column 90
[14] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9222 - 9224
[15] Patent: WO2014/418, 2014, A1, . Location in patent: Page/Page column 60
[16] RSC Advances, 2014, vol. 4, # 84, p. 44629 - 44633
[17] Patent: US2015/197511, 2015, A1, . Location in patent: Paragraph 0294; 0295
[18] European Journal of Organic Chemistry, 2015, vol. 2015, # 26, p. 5775 - 5780
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Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 14, p. 4396 - 4401
[2] Tetrahedron, 1997, vol. 53, # 48, p. 16521 - 16532
[3] Journal of the American Chemical Society, 1983, vol. 105, # 1, p. 74 - 79
[4] Journal of the American Chemical Society, 1937, vol. 59, p. 2348,2350
[5] Patent: WO2014/418, 2014, A1,
[6] Patent: WO2014/106238, 2014, A1,
[7] RSC Advances, 2014, vol. 4, # 84, p. 44629 - 44633
[8] Patent: US2015/197511, 2015, A1,
[9] European Journal of Organic Chemistry, 2017, vol. 2017, # 14, p. 1889 - 1893
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  • [ 30095-98-8 ]
  • [ 59-48-3 ]
  • [ 35613-44-6 ]
Reference: [1] Liebigs Annalen der Chemie, 1985, vol. 1985, # 7, p. 1398 - 1412
[2] Organic Letters, 2009, vol. 11, # 6, p. 1345 - 1348
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  • [ 347877-90-1 ]
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Reference: [1] Tetrahedron, 2008, vol. 64, # 23, p. 5531 - 5540
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  • [ 67-56-1 ]
  • [ 3342-78-7 ]
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Reference: [1] Patent: US2008/312231, 2008, A1, . Location in patent: Page/Page column 37
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  • [ 15307-79-6 ]
Reference: [1] Patent: CN108947861, 2018, A,
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  • [ 35613-44-6 ]
  • [ 79099-07-3 ]
  • [ 400797-94-6 ]
YieldReaction ConditionsOperation in experiment
42%
Stage #1: With acetic acid In dichloromethane at 20℃; for 2 h;
Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 40℃;
Preparation of tert-butyl 4-(2-oxoindolin- 1 -yl)piperidine- 1 -carboxylate (Compound 6-2) [00232j A mixture of Compound 6-1 (3.30 g, 20 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (4.38 g, 22 mmol), acetic acid (HOAc, 600 mg, 10 mmol) in dichloromethane (DCM, 80 mL) was stirred at room temperature for 2 h, then sodium triacetoxyborohydride (6.36 g, 30 mmol) was added in portions and heated to 40°C, stirred overnight. The reaction mixture was cooled to room temperature and diluted with dichloromethane (200 mL), washed with water (200 mL x 2) and sodium bicarbonate (sat. aq., 200 mL x 2), dried over anhydrous sodium sulfate, concentrated to give the crude product, purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 5percent, V/v) to give Compound 6-2 (2.65 g, yield: 42percent) as a white solid. MS (ES): mlz: 261[M+H-56]. ‘H NMR (400 MHz, CDC13) ö: 7.24 (m, 2H), 7.01 (m, 2H), 4.41 (m, 1H), 4.28 (br s, 2H), 3.53 (s, 2H), 2.83 (br s, 2H), 2.32 (m, 2H), 1.70 (m, 2H), 1.50 (s, 9H).
42%
Stage #1: With acetic acid In dichloromethane at 20℃; for 2 h;
Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 40℃;
Preparation of tert-butyl 4-(2-oxoindolin- 1 -yl)piperidine- 1 -carboxylate (Compound 11-4) [00270j A mixture of methyl 2-(2-aminophenyl)acetate (Compound 11-3, 3.30 g, 20 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (4.38 g, 22 mmol), acetic acid (HOAc, 600 mg, 10 mmol) in dichloromethane (DCM, 80 mL) was stirred at room temperature for 2 h, then sodium triacetoxyborohydride (NaBH(OAc)3, 6.36 g, 30 mmol) was added in portions and heated to 40°C, stirred overnight. The reaction mixture was cooled to room temperature and diluted with dichloromethane (DCM, 200 mL), washed with water (200 mL x 2) and sodium bicarbonate (sat. aq., 200 mL x 2), dried over anhydrous sodium sulfate, concentrated to give the crude product, purified by flash colunm chromatography on silica gel (ethyl acetate petroleum ether, 1 20-1 15-1 10 v v) to give the desired product tert-butyl 4-(2-oxoindolin- 1 -yl)piperidine- 1- carboxylate (Compound 11-4, 2.65 g, yield: 42percent) as a pale yellow solid. MS (ESI):mlz: 261[M+H-56]. ‘H NMR (400 MHz, CDC13) ö: 7.24 (m, 2H), 7.01 (m, 2H), 4.41 (m, 1H), 4.28 (br s, 2H), 3.53 (s, 2H), 2.83 (br s, 2H), 2.32 (m, 2H), 1.70 (m, 2H), 1.50 (s, 9H).
62% With sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; acetic acid In dichloromethane C.
4-(2-Oxo-2.3-dihydro-indol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester.
Methyl 2-aminophenylacetate (3.0 g, 18.2 mmol) and 1-tert-butoxycarbonyl-4-piperidone (4.5 g, 22.6 mmol) were set stirring in 50 mL of CH2Cl2 under an atmosphere of nitrogen.
Sodium triacetoxyborohydride (5.4 g, 25.5 mmol) was added followed by 1 mL of acetic acid.
After 20 h at rt the mixture was quenched by the slow addition of saturated NaHCO3.
After stirring for 30 min, the organics were separated, dried (MgSO4), and evaporated to afford 7.5 g of a purple oil.
Purification by column chromatography (silica, 10-50percent EtOAc/hexanes) gave 3.9 g (62percent) of the title compound. TLC (silica, 25percent EtOAc/hexanes): Rf=0.15. 1H NMR (400MHz, CDCl3): 7.25 (m, 2H), 7.01 (m, 2H), 4.40 (m, 1H), 3.53 (s, 2H), 2.83 (m, 2H), 2.32 (m, 2H), 1.70 (m, 2H), 1.51 (s, 9H).
Reference: [1] Patent: WO2014/106238, 2014, A1, . Location in patent: Paragraph 00232; 00314; 00341; 00365; 00398; 00499
[2] Patent: WO2014/106238, 2014, A1, . Location in patent: Paragraph 00270
[3] Patent: US2005/101587, 2005, A9,
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