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Product Details of [ 29681-78-5 ]

CAS No. :29681-78-5 MDL No. :MFCD24549983
Formula : C9H15NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :JMCYIDYGZXGWNJ-UHFFFAOYSA-N
M.W : 185.22 Pubchem ID :13584855
Synonyms :

Safety of [ 29681-78-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 29681-78-5 ]

* 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 [ 29681-78-5 ]

[ 29681-78-5 ] Synthesis Path-Downstream   1~50

  • 1
  • 2-(2-Azido-ethyl)-2-methyl-malonic acid diethyl ester [ No CAS ]
  • [ 29681-78-5 ]
YieldReaction ConditionsOperation in experiment
90% With triphenylphosphine In tetrahydrofuran; water Ambient temperature;
  • 2
  • [ 10444-11-8 ]
  • [ 29681-78-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogen at 50℃;
  • 3
  • [ 368-39-8 ]
  • [ 29681-78-5 ]
  • [ 27768-58-7 ]
YieldReaction ConditionsOperation in experiment
71.5% In dichloromethane for 15h;
  • 4
  • [ 100-39-0 ]
  • [ 29681-78-5 ]
  • [ 1026945-23-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; sodium iodide In tetrahydrofuran; paraffin 1.) reflux, 1 h, 2.) reflux, 4 h;
  • 5
  • [ 5162-44-7 ]
  • [ 29681-78-5 ]
  • [ 1026249-14-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; sodium iodide In tetrahydrofuran; paraffin Heating; 1.) 1 h, 2.) 2 h;
  • 6
  • [ 29681-78-5 ]
  • [ 1119-51-3 ]
  • [ 1026703-24-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; sodium iodide In tetrahydrofuran; paraffin Heating; 1.) 1 h, 2.) 2 h;
  • 7
  • [ 3731-16-6 ]
  • [ 74-88-4 ]
  • [ 29681-78-5 ]
YieldReaction ConditionsOperation in experiment
46% Into a 500-mL 3-necked round-bottom flask under nitrogen, was placed 124.1 (20 g, 116.83 mmol, 1.00 equiv) in THF (200 mL). This was followed by the addition of n-BuLi (51.5 mL, 1.10 equiv, 2.5M) dropwise with stirring at -78 C. The reaction was stirred for 1 hour at ambient temperature. To the mixture was added Mel (18.3 g, 1.10 equiv) dropwise with stirring at -78 C. The reaction was stirred overnight at room temperature, and then quenched by the addition of 300 mL of NH4C 1 (aq). The resulting solution was extracted with 2 x 250 mL of CH2C12, organic layers were combined and concentrated under vacuum. The crude product was re-crystallized from EtOAc/n-hexane to provide 10.0 g (46.0 %) of 124.2 as a white solid.
With sodium; for 1h;Reflux; To a stirred solution of sodium (247 mg, 10.75 mmol) in 10 mL of absolute ethanol ethyl 3-methyl-2-oxopiperidine-3-carboxylate (1.84 g, 10.75 mmol) and methyl iodide (0,736 mL, 11.83 mmol) were added. The reaction mixture was heated at reflux for 1 h and afterwards diluted with 30 mL of water. Obtained solution was extracted with dichloromethane (2x30 mL). Separated organic phase was dried over Na2SO3, filtered and concentrated under reduced pressure. The crude ethyl 3-methyl-2 oxopiperidine-3-carboxylate (1.61 g) was stirred for 1 h with sodium hydride (310 mg, 80% suspension in mineral oil ) in 20 mL of anhydrous N-methylpyrrolidone. 1-Fluoro-4-nitrobenzen (1.23 g, 8.7 mmol) was added and the mixture was stirred for 18 h at room temperature. After completion reaction mixture was diluted with 50 mL of water and extracted with EtOAc. Separated organic phase was dried over Na2SO3, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography using EtOAc/hexane (1/2) as eluant to obtain 1e as yellow oil, yield: 1.54 g.
  • 8
  • [ 29681-78-5 ]
  • [ 1026303-26-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaH, NaI / tetrahydrofuran; paraffin / Heating; 1.) 1 h, 2.) 2 h 2: 3M KOH / methanol / 10 h / Ambient temperature
  • 9
  • [ 29681-78-5 ]
  • [ 188885-23-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaH, NaI / tetrahydrofuran; paraffin / Heating; 1.) 1 h, 2.) 2 h 2: 3M KOH / methanol / 10 h / Ambient temperature
  • 10
  • [ 29681-78-5 ]
  • [ 1027021-45-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaH, NaI / tetrahydrofuran; paraffin / 1.) reflux, 1 h, 2.) reflux, 4 h 2: 3N KOH / methanol / 10 h / Ambient temperature
  • 11
  • [ 29681-78-5 ]
  • [ 1026406-08-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaH, NaI / tetrahydrofuran; paraffin / Heating; 1.) 1 h, 2.) 2 h 2: 3M KOH / methanol / 10 h / Ambient temperature 3: 1.) oxalyl chloride, DMF, 2.) n-BuMgCl / 1.) Et2O, room temperature, 30 min, 2.) CH2Cl2, THF, 0 deg C, 1 h
  • 12
  • [ 29681-78-5 ]
  • [ 188885-24-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaH, NaI / tetrahydrofuran; paraffin / Heating; 1.) 1 h, 2.) 2 h 2: 3M KOH / methanol / 10 h / Ambient temperature 3: 1.) oxalyl chloride, DMF, 2.) n-BuMgCl / 1.) Et2O, room temperature, 30 min, 2.) CH2Cl2, THF, 0 deg C, 1 h
  • 13
  • [ 29681-78-5 ]
  • 3-[3-methyl-2-oxo-1-(3-butenyl)piperidin-3-yl]-2-diazo-3-oxopropionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NaH, NaI / tetrahydrofuran; paraffin / Heating; 1.) 1 h, 2.) 2 h 2: 3M KOH / methanol / 10 h / Ambient temperature 3: 1.) oxalyl chloride, DMF, 2.) n-BuMgCl / 1.) Et2O, room temperature, 30 min, 2.) CH2Cl2, THF, 0 deg C, 1 h 4: 62 percent / Et3N, MsN3 / acetonitrile / 3 h / Ambient temperature
  • 14
  • [ 29681-78-5 ]
  • [ 1027037-55-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaH, NaI / tetrahydrofuran; paraffin / 1.) reflux, 1 h, 2.) reflux, 4 h 2: 3N KOH / methanol / 10 h / Ambient temperature 3: 1.) oxalyl chloride, DMF, 2.) n-BuMgCl / 1.) Et2O, room temperature, 30 min, 2.) CH2Cl2, THF, 0 deg C, 1 h
  • 15
  • [ 29681-78-5 ]
  • [ 188885-25-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NaH, NaI / tetrahydrofuran; paraffin / Heating; 1.) 1 h, 2.) 2 h 2: 3M KOH / methanol / 10 h / Ambient temperature 3: 1.) oxalyl chloride, DMF, 2.) n-BuMgCl / 1.) Et2O, room temperature, 30 min, 2.) CH2Cl2, THF, 0 deg C, 1 h 4: 70 percent / Et3N, MsN3 / acetonitrile / 3 h / Ambient temperature
  • 16
  • [ 29681-78-5 ]
  • [ 188885-04-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NaH, NaI / tetrahydrofuran; paraffin / 1.) reflux, 1 h, 2.) reflux, 4 h 2: 3N KOH / methanol / 10 h / Ambient temperature 3: 1.) oxalyl chloride, DMF, 2.) n-BuMgCl / 1.) Et2O, room temperature, 30 min, 2.) CH2Cl2, THF, 0 deg C, 1 h 4: 85 percent / Et3N, MsN3 / acetonitrile / 3 h / Ambient temperature
  • 17
  • [ 29681-78-5 ]
  • 2-(4-pentenyl)-6-methyl-7-oxo-11-oxa-2-azatricyclo[6.2.1.01,6]undec-9-ene-8,9,10-tricarboxylic acid 8-methyl ester 9,10-dimethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: NaH, NaI / tetrahydrofuran; paraffin / Heating; 1.) 1 h, 2.) 2 h 2: 3M KOH / methanol / 10 h / Ambient temperature 3: 1.) oxalyl chloride, DMF, 2.) n-BuMgCl / 1.) Et2O, room temperature, 30 min, 2.) CH2Cl2, THF, 0 deg C, 1 h 4: 70 percent / Et3N, MsN3 / acetonitrile / 3 h / Ambient temperature 5: 78 percent / rhodium(II) acetate / benzene / 2 h / Heating
  • 18
  • [ 29681-78-5 ]
  • 1-benzyl-6,9b-epoxy-4a-methyl-5,7,9-trioxo-8-phenyldodecahydropyrrolo[3,4]quinoline-6-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: NaH, NaI / tetrahydrofuran; paraffin / 1.) reflux, 1 h, 2.) reflux, 4 h 2: 3N KOH / methanol / 10 h / Ambient temperature 3: 1.) oxalyl chloride, DMF, 2.) n-BuMgCl / 1.) Et2O, room temperature, 30 min, 2.) CH2Cl2, THF, 0 deg C, 1 h 4: 85 percent / Et3N, MsN3 / acetonitrile / 3 h / Ambient temperature 5: 83 percent / rhodium(II) acetate / benzene / 2 h / Heating
  • 19
  • [ 29681-78-5 ]
  • 2-benzyl-6-methyl-7-oxo-11-oxa-2-azatricyclo[6.2.1.01,6]undec-9-ene-8,9,10-tricarboxylic acid 8-ethyl ester 9,10-dimethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: NaH, NaI / tetrahydrofuran; paraffin / 1.) reflux, 1 h, 2.) reflux, 4 h 2: 3N KOH / methanol / 10 h / Ambient temperature 3: 1.) oxalyl chloride, DMF, 2.) n-BuMgCl / 1.) Et2O, room temperature, 30 min, 2.) CH2Cl2, THF, 0 deg C, 1 h 4: 85 percent / Et3N, MsN3 / acetonitrile / 3 h / Ambient temperature 5: 80 percent / rhodium(II) acetate / benzene / 2 h / Heating
  • 20
  • [ 29681-78-5 ]
  • 2-Amino-4a-methyl-4a,5,6,7-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 71.5 percent / CH2Cl2 / 15 h 2: 3.4 g / sodium ethanolate / ethanol / 24 h / Heating
  • 21
  • [ 609-08-5 ]
  • [ 29681-78-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1) NaOH / 1) THF, 0 deg C; 2) room temp., 12 h 2: 90 percent / Ph3P / H2O; tetrahydrofuran / Ambient temperature
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 16 h / 70 °C 2.1: hydrazine hydrate / ethanol / 16 h / 80 °C
  • 22
  • [ 29681-78-5 ]
  • [ 350-46-9 ]
  • [ 1444001-21-1 ]
YieldReaction ConditionsOperation in experiment
1.54 g Stage #1: 3-methyl-2-oxopiperidine-3-carboxylic acid ethyl ester With sodium hydride In 1-methyl-pyrrolidin-2-one; mineral oil for 1h; Stage #2: 4-Fluoronitrobenzene In 1-methyl-pyrrolidin-2-one; mineral oil at 20℃; for 18h; Ethyl 3-methyl-1-(4-nitrophenyl)-2-oxopiperidine-3-carboxylate (1e) To a stirred solution of sodium (247 mg, 10.75 mmol) in 10 mL of absolute ethanol ethyl 3-methyl-2-oxopiperidine-3-carboxylate (1.84 g, 10.75 mmol) and methyl iodide (0,736 mL, 11.83 mmol) were added. The reaction mixture was heated at reflux for 1 h and afterwards diluted with 30 mL of water. Obtained solution was extracted with dichloromethane (2x30 mL). Separated organic phase was dried over Na2SO3, filtered and concentrated under reduced pressure. The crude ethyl 3-methyl-2 oxopiperidine-3-carboxylate (1.61 g) was stirred for 1 h with sodium hydride (310 mg, 80% suspension in mineral oil ) in 20 mL of anhydrous N-methylpyrrolidone. 1-Fluoro-4-nitrobenzen (1.23 g, 8.7 mmol) was added and the mixture was stirred for 18 h at room temperature. After completion reaction mixture was diluted with 50 mL of water and extracted with EtOAc. Separated organic phase was dried over Na2SO3, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography using EtOAc/hexane (1/2) as eluant to obtain 1e as yellow oil, yield: 1.54 g. 1H NMR (CDCl3) δ 1.31 (t, 3H, J = 7.1 Hz, CH2CH3), 1.57 (s, 3H, CH3), 1.86-2.14 (m, 3H, COCHCH2, NCH2CH2), 2.41-2.49 (m, 1H, COCHCH2), 3.69-3.87 (m, 2H, NCH2), 4.17-4.33 (m, 2H, CH2CH3), 7.49 (d, 2H, J = 9.1 Hz, Ar-H2,H6), 8.23 (d, 2H, J = 9.1 Hz, Ar-H3,H5). MS (ESI) (%) = 307.1 (M+, 15), 193.1 (97), 155.0 (98), 91.1 (100). HRMS (ESI) calcd for C15H19N2O5 307.1294, found 307.1301. IR (ATR) 2981, 2940, 1728, 1656, 1591, 1517, 1495, 1458, 1427, 1407, 1340, 1316, 1246, 1192, 1177, 1132, 1039 cm-1.
  • 23
  • [ 29681-78-5 ]
  • [ 1444001-32-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 1 h 1.2: 18 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr 3.1: ethanol / 15 h / Reflux 4.1: dmap / tetrahydrofuran / 15 h / 60 °C
  • 24
  • [ 29681-78-5 ]
  • [ 1444001-37-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 1 h 1.2: 18 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr 3.1: ethanol / 15 h / Reflux 4.1: dmap / tetrahydrofuran / 15 h / 60 °C 5.1: hydrazine hydrate / ethanol / 2.5 h / 0 - 80 °C
  • 25
  • [ 29681-78-5 ]
  • [ 1444001-42-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 1 h 1.2: 18 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr 3.1: ethanol / 15 h / Reflux 4.1: dmap / tetrahydrofuran / 15 h / 60 °C 5.1: hydrazine hydrate / ethanol / 2.5 h / 0 - 80 °C 6.1: triethylamine / dichloromethane / 15 h / 0 - 20 °C
  • 26
  • [ 29681-78-5 ]
  • ethyl 1-(4-((S)-5-((2-aminothiazole-5-carboxamido)methyl)-2-oxooxazolidin-3-yl)phenyl)-3-methyl-2-oxopiperidine-3-carboxylate trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 1 h 1.2: 18 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr 3.1: ethanol / 15 h / Reflux 4.1: dmap / tetrahydrofuran / 15 h / 60 °C 5.1: hydrazine hydrate / ethanol / 2.5 h / 0 - 80 °C 6.1: triethylamine / dichloromethane / 15 h / 0 - 20 °C 7.1: dichloromethane / 15 h / 0 - 20 °C
  • 27
  • [ 29681-78-5 ]
  • 1-(4-((S)-5-((2-aminothiazole-5-carboxamido)methyl)-2-oxooxazolidin-3-yl)phenyl)-3-methyl-2-oxopiperidine-3-carboxylic acid trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 1 h 1.2: 18 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr 3.1: ethanol / 15 h / Reflux 4.1: dmap / tetrahydrofuran / 15 h / 60 °C 5.1: hydrazine hydrate / ethanol / 2.5 h / 0 - 80 °C 6.1: triethylamine / dichloromethane / 15 h / 0 - 20 °C 7.1: lithium hydroxide; water / methanol / 15 h / 20 °C 8.1: dichloromethane / 15 h / 0 - 20 °C
  • 28
  • [ 29681-78-5 ]
  • C26H31N5O8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 1 h 1.2: 18 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr 3.1: ethanol / 15 h / Reflux 4.1: dmap / tetrahydrofuran / 15 h / 60 °C 5.1: hydrazine hydrate / ethanol / 2.5 h / 0 - 80 °C 6.1: triethylamine / dichloromethane / 15 h / 0 - 20 °C 7.1: lithium hydroxide; water / methanol / 15 h / 20 °C
  • 29
  • [ 29681-78-5 ]
  • [ 1444001-23-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 1 h 1.2: 18 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr
  • 30
  • [ 29681-78-5 ]
  • [ 1444001-27-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 1 h 1.2: 18 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 760.05 Torr 3.1: ethanol / 15 h / Reflux
  • 31
  • [ 29681-78-5 ]
  • C15H19NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3
  • 32
  • [ 29681-78-5 ]
  • C19H28N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3 3.1: diphenyl phosphoryl azide; triethylamine / 36 h / 0 °C / Inert atmosphere; Reflux
  • 33
  • [ 29681-78-5 ]
  • C14H20N2O2*(x)ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3 3.1: diphenyl phosphoryl azide; triethylamine / 36 h / 0 °C / Inert atmosphere; Reflux 4.1: hydrogenchloride / dichloromethane / 3 h / 20 °C
  • 34
  • [ 29681-78-5 ]
  • C25H30N6O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3 3.1: diphenyl phosphoryl azide; triethylamine / 36 h / 0 °C / Inert atmosphere; Reflux 4.1: hydrogenchloride / dichloromethane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0.5 h / -20 - 0 °C / Inert atmosphere 5.2: 0.5 h / 20 °C
  • 35
  • [ 29681-78-5 ]
  • C23H24N6O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3 3.1: diphenyl phosphoryl azide; triethylamine / 36 h / 0 °C / Inert atmosphere; Reflux 4.1: hydrogenchloride / dichloromethane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0.5 h / -20 - 0 °C / Inert atmosphere 5.2: 0.5 h / 20 °C 6.1: sodium; ethanol / 0.5 h / Inert atmosphere; Reflux
  • 36
  • [ 29681-78-5 ]
  • C15H16N6O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3 3.1: diphenyl phosphoryl azide; triethylamine / 36 h / 0 °C / Inert atmosphere; Reflux 4.1: hydrogenchloride / dichloromethane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0.5 h / -20 - 0 °C / Inert atmosphere 5.2: 0.5 h / 20 °C 6.1: sodium; ethanol / 0.5 h / Inert atmosphere; Reflux 7.1: trifluoroacetic acid / 7 h / 100 °C / Inert atmosphere
  • 37
  • [ 29681-78-5 ]
  • C27H31FN6O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3 3.1: diphenyl phosphoryl azide; triethylamine / 36 h / 0 °C / Inert atmosphere; Reflux 4.1: hydrogenchloride / dichloromethane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0.5 h / -20 - 0 °C / Inert atmosphere 5.2: 0.5 h / 20 °C 6.1: sodium; ethanol / 0.5 h / Inert atmosphere; Reflux 7.1: trifluoroacetic acid / 7 h / 100 °C / Inert atmosphere 8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
  • 38
  • [ 29681-78-5 ]
  • 1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(2-methoxy-ethoxy)ethyl)-5-methyl-3-((R)-3-methyl-2-oxopiperidin-3-yl)-6-(2H-1,2,3-triazol-2-yl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione [ No CAS ]
  • 1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(2-methoxy-ethoxy)ethyl)-5-methyl-3-((S)-3-methyl-2-oxopiperidin-3-yl)-6-(2H-1,2,3-triazol-2-yl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3 3.1: diphenyl phosphoryl azide; triethylamine / 36 h / 0 °C / Inert atmosphere; Reflux 4.1: hydrogenchloride / dichloromethane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0.5 h / -20 - 0 °C / Inert atmosphere 5.2: 0.5 h / 20 °C 6.1: sodium; ethanol / 0.5 h / Inert atmosphere; Reflux 7.1: trifluoroacetic acid / 7 h / 100 °C / Inert atmosphere 8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 9.1: Resolution of racemate
  • 39
  • [ 29681-78-5 ]
  • C42H47FN6O6SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3 3.1: diphenyl phosphoryl azide; triethylamine / 36 h / 0 °C / Inert atmosphere; Reflux 4.1: hydrogenchloride / dichloromethane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0.5 h / -20 - 0 °C / Inert atmosphere 5.2: 0.5 h / 20 °C 6.1: sodium; ethanol / 0.5 h / Inert atmosphere; Reflux 7.1: trifluoroacetic acid / 7 h / 100 °C / Inert atmosphere 8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
  • 40
  • [ 29681-78-5 ]
  • C28H33FN6O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3 3.1: diphenyl phosphoryl azide; triethylamine / 36 h / 0 °C / Inert atmosphere; Reflux 4.1: hydrogenchloride / dichloromethane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0.5 h / -20 - 0 °C / Inert atmosphere 5.2: 0.5 h / 20 °C 6.1: sodium; ethanol / 0.5 h / Inert atmosphere; Reflux 7.1: trifluoroacetic acid / 7 h / 100 °C / Inert atmosphere 8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 9.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 9.2: 2 h / 20 °C
  • 41
  • [ 29681-78-5 ]
  • C43H49FN6O6SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3 3.1: diphenyl phosphoryl azide; triethylamine / 36 h / 0 °C / Inert atmosphere; Reflux 4.1: hydrogenchloride / dichloromethane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0.5 h / -20 - 0 °C / Inert atmosphere 5.2: 0.5 h / 20 °C 6.1: sodium; ethanol / 0.5 h / Inert atmosphere; Reflux 7.1: trifluoroacetic acid / 7 h / 100 °C / Inert atmosphere 8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 9.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 9.2: 2 h / 20 °C
  • 42
  • [ 29681-78-5 ]
  • 3-((R)-1,3-dimethyl-2-oxopiperidin-3-yl)-1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(2-methoxyethoxy)ethyl)-5-methyl-6-(2H-1,2,3-triazol-2-yl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione [ No CAS ]
  • 3-((S)-1,3-dimethyl-2-oxopiperidin-3-yl)-1-((R)-2-(5-fluoro-2-methoxyphenyl)-2-(2-methoxyethoxy)ethyl)-5-methyl-6-(2H-1,2,3-triazol-2-yl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere 1.2: 20 °C 2.1: sodium hydroxide; water / ethanol / 20 °C 2.2: pH 2-3 3.1: diphenyl phosphoryl azide; triethylamine / 36 h / 0 °C / Inert atmosphere; Reflux 4.1: hydrogenchloride / dichloromethane / 3 h / 20 °C 5.1: triethylamine / dichloromethane / 0.5 h / -20 - 0 °C / Inert atmosphere 5.2: 0.5 h / 20 °C 6.1: sodium; ethanol / 0.5 h / Inert atmosphere; Reflux 7.1: trifluoroacetic acid / 7 h / 100 °C / Inert atmosphere 8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 9.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 9.2: 2 h / 20 °C 10.1: Resolution of racemate
  • 43
  • [ 2746-25-0 ]
  • [ 29681-78-5 ]
  • C17H23NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 3-methyl-2-oxopiperidine-3-carboxylic acid ethyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: p-Methoxybenzyl bromide In N,N-dimethyl-formamide at 20℃; 124 Synthesis of compound 124.3. Into a 250-mL 3-necked round-bottom flask under nitrogen, was placed 124.3 (10.0 g, 53.99 mmol, 1.00 equiv) in DMF (100 mL). This was followed by the addition of NaH (2.59 g, 107.92 mmol, 1.20 equiv) in portions at 0 °C. The resulting solution was stirred for 30 min at 0 °C in a water/ice bath. To this was added 1- (bromomethyl)-4-methoxybenzene (16.22 g, 80.67 mmol, 1.50 equiv). The reaction was stirred overnight at room temperature. The reaction was then quenched by the addition of 300 mL of H4C 1 (aq). The resulting solution was extracted with 2 x 500 mL of EtOAc. Organic layers combined and concentrated under vacuum. The crude was purified by column chromatography to provide 14.5 g (88.0 %) of 124.3 as a yellow liquid.
  • 44
  • [ 29681-78-5 ]
  • [ 89775-75-7 ]
YieldReaction ConditionsOperation in experiment
62% With lithium hydroxide In methanol; water at 20℃; for 22h; Inert atmosphere;
112 mg With sodium hydroxide In methanol; water at 25℃; for 3h; 19 3-Methyl-2-oxo-piperidine-3-carboxylic acid To a solution of ethyl 3-methyl-2-oxo-piperidine-3-carboxylate (150 mg, 0.80 mmol, 1 eq) in MeOH (3 mL) and H2O (0.6 mL) was added NaOH (161.9 mg, 4.05 mmol, 5 eq), and then the reaction mixture was stirred at 25 °C for 3 hours. The reaction was adjusted with HCl (2 M) to pH = 5, and then the mixture was concentrated under reduced pressure. The residue was washed with DCM: MeOH = 10:1 (30 mL) and filtered, the filtrate was concentrated under reduce pressure to give 3-nethyl-2-oxo-piperidine-3-carboxylic acid (112 mg, 0.71 mmol, 87.9% yield) was obtained as a white solid.
  • 45
  • [ 63399-70-2 ]
  • [ 29681-78-5 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate In ethanol at 80℃; for 16h; 19 Ethyl 3-methyl-2-oxo-piperidine-3-carboxylate To a solution of diethyl 2-[3-(1,3-dioxoisoindolin-2-yl)propyl]-2-methyl-propanedioate (1 g, 2.77 mmol, 1 eq) in EtOH (25 mL) was added NH2NH2.H2O (162.9 mg, 2.77 mmol, 0.15 mL, 85%, 1 eq), and then the mixture was stirred at 80 °C for 16 hours. The reaction mixture was filtered and the filtrate was concentrated under reduce pressure. The residue was purified by column chromatography over silica gel to afford ethyl 3-methyl-2-oxo-piperidine-3-carboxylate (150 mg, crude) as a white solid.
  • 46
  • [ 29681-78-5 ]
  • (S)-3-methyl-3-(5-(2-((4-(trifluoromethyl)phenyl)amino)pyridin-3-yl)-1,3,4-oxadiazol-2-yl)piperidin-2-one [ No CAS ]
  • (R)-3-methyl-3-(5-(2-((4-(trifluoromethyl)phenyl)amino)pyridin-3-yl)-1,3,4-oxadiazol-2-yl)piperidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydroxide / methanol; water / 3 h / 25 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 3: triethylamine; p-toluenesulfonyl chloride / dichloromethane / 2 h / 20 °C 4: ammonium hydroxide / ethanol / Resolution of racemate
  • 47
  • [ 29681-78-5 ]
  • C20H20F3N5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol; water / 3 h / 25 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C
  • 48
  • [ 29681-78-5 ]
  • 3-methyl-3-(5-(2-((4-(trifluoromethyl)phenyl)amino)pyridin-3-yl)-1,3,4-oxadiazol-2-yl)piperidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / methanol; water / 3 h / 25 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C 3: triethylamine; p-toluenesulfonyl chloride / dichloromethane / 2 h / 20 °C
  • 49
  • [ 29681-78-5 ]
  • N'-(3-methyl-2-oxo-piperidine-3-carbonyl)-2-[4-(pentafluoro-λ6-sulfanyl)anilino]pyridine-3-carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol; water / 3 h / 25 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 2 h / 25 °C
  • 50
  • [ 29681-78-5 ]
  • 3-methyl-3-[5-[2-[4-(pentafluoro-λ6-sulfanyl)anilino]-3-pyridyl]-1,3,4-oxadiazol-2-yl]piperidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / methanol; water / 3 h / 25 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 2 h / 25 °C 3: triethylamine; p-toluenesulfonyl chloride / dichloromethane / 1 h / 25 °C
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