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Chemical Structure| 1356476-38-4
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Product Details of [ 1356476-38-4 ]

CAS No. :1356476-38-4 MDL No. :MFCD28502553
Formula : C14H23NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 237.34 Pubchem ID :-
Synonyms :

Safety of [ 1356476-38-4 ]

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Application In Synthesis of [ 1356476-38-4 ]

* 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 [ 1356476-38-4 ]

[ 1356476-38-4 ] Synthesis Path-Downstream   1~25

  • 2
  • [ 1356476-38-4 ]
  • [ 1346556-74-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dihydrogen peroxide 2: Dess-Martin periodane / dichloromethane 3: potassium <i>tert</i>-butylate / tetrahydrofuran
  • 3
  • [ 1356476-38-4 ]
  • [ 1346556-75-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: dihydrogen peroxide 2: Dess-Martin periodane / dichloromethane 3: potassium <i>tert</i>-butylate / tetrahydrofuran 4: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 1034.32 Torr 5: hydrogenchloride; water / 1,4-dioxane; dichloromethane 6: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C
  • 4
  • [ 1356476-38-4 ]
  • [ 1356476-76-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dihydrogen peroxide 2: Dess-Martin periodane / dichloromethane 3: potassium <i>tert</i>-butylate / tetrahydrofuran 4: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 1034.32 Torr
  • 5
  • [ 1356476-38-4 ]
  • C22H25F3N2O*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dihydrogen peroxide 2: Dess-Martin periodane / dichloromethane 3: potassium <i>tert</i>-butylate / tetrahydrofuran 4: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 1034.32 Torr 5: hydrogenchloride; water / 1,4-dioxane; dichloromethane
  • 7
  • [ 1779-49-3 ]
  • [ 203661-69-2 ]
  • [ 1356476-38-4 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: Methyltriphenylphosphonium bromide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Step 1 - Tert-butyl 2-methylene-7-azaspiror3.51nonane-7-carboxylate To a solution of methyl(triphenyl)phosphonium-bromide (19.4 g, 54.3 mmol) in THF (100 mL) was added t-BuOK (7.03 g, 62.6 mmol) at 0 °C dropwise. After the reaction mixture was stirred at 0 °C for 0.5 hr, a solution oftert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate (10.0 g, 41.7 mmol, CAS 203661-69-2) in THF (30 mL) was added at 0 °C. Then the reaction mixture was warmed to 20 °C and stirred for 1 hr. On completion, the reaction mixture was poured into saturated NH4CI (200 mL) and extracted with EA (3 X 90 mL). The combined organic layers were washed with brine (2 x 50 mL), dried over Na2SC>4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE: EA= 80: 1) to give the title compound (8.40 g, 84% yield) as colorless oil. TlNMR^OO MHz, CDCF) 54.83 (d, J= 2.0 Hz, 2H), 3.39 - 3.25 (m, 4H), 2.43 (d, J= 1.2 Hz, 4H), 1.59 - 1.52 (m, 4H), 1.46 (s, 9H).
39% With potassium <i>tert</i>-butylate In tetrahydrofuran
  • 8
  • [ 1356476-38-4 ]
  • [ 73183-34-3 ]
  • [ 1422558-39-1 ]
YieldReaction ConditionsOperation in experiment
71% With iron(III) paratoluenesulfonate; lithium tert-butoxide In 1-methyl-pyrrolidin-2-one at 80℃; for 18h; Inert atmosphere;
  • 9
  • [ 1779-49-3 ]
  • tert-butyl 2-oxo-9-azadispiro[3.1.56.14]dodecane-9-carboxylate [ No CAS ]
  • [ 1356476-38-4 ]
YieldReaction ConditionsOperation in experiment
92% With potassium <i>tert</i>-butylate In diethyl ether at 0 - 20℃; for 1h; Inert atmosphere;
  • 10
  • [ 1356476-38-4 ]
  • (1R*,2R*)-tert-butyl 1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9azadispiro[3.1.56.14]dodecane-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: zinc copper / 1,2-dimethoxyethane / 16 h / 0 - 20 °C / Inert atmosphere 2: ammonium chloride; zinc / methanol / 16 h / 20 °C 3: sodium tetrahydroborate; methanol / 12 h / 0 - 20 °C 4: triethylamine / water; dichloromethane / 20 h / 0 - 20 °C 5: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 4 h / 20 °C / Inert atmosphere 6: sodium methylate / methanol / 16 h / 70 °C / Inert atmosphere; Glovebox; Sealed tube
  • 11
  • [ 1356476-38-4 ]
  • C16H27NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: zinc copper / 1,2-dimethoxyethane / 16 h / 0 - 20 °C / Inert atmosphere 2: ammonium chloride; zinc / methanol / 16 h / 20 °C 3: sodium tetrahydroborate; methanol / 12 h / 0 - 20 °C
  • 12
  • [ 1356476-38-4 ]
  • tert-butyl 9-azadispiro[3.1.56.14]dodec-1-ene-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: zinc copper / 1,2-dimethoxyethane / 16 h / 0 - 20 °C / Inert atmosphere 2: ammonium chloride; zinc / methanol / 16 h / 20 °C 3: sodium tetrahydroborate; methanol / 12 h / 0 - 20 °C 4: triethylamine / water; dichloromethane / 20 h / 0 - 20 °C 5: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 4 h / 20 °C / Inert atmosphere
  • 13
  • [ 1356476-38-4 ]
  • tert-butyl 2-oxo-9-azadispiro[3.1.56.14]dodecane-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: zinc copper / 1,2-dimethoxyethane / 16 h / 0 - 20 °C / Inert atmosphere 2: ammonium chloride; zinc / methanol / 16 h / 20 °C
  • 14
  • [ 1356476-38-4 ]
  • tert-butyl 2-(tosyloxy)-9-azadispiro[3.1.56.14]dodecane-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: zinc copper / 1,2-dimethoxyethane / 16 h / 0 - 20 °C / Inert atmosphere 2: ammonium chloride; zinc / methanol / 16 h / 20 °C 3: sodium tetrahydroborate; methanol / 12 h / 0 - 20 °C 4: triethylamine / water; dichloromethane / 20 h / 0 - 20 °C
  • 15
  • [ 1356476-38-4 ]
  • [ 76-02-8 ]
  • C16H23Cl2NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With zinc copper In 1,2-dimethoxyethane at 0 - 20℃; for 16h; Inert atmosphere;
  • 16
  • [ 1356476-38-4 ]
  • benzyl 2-(2-aminoethyl)-9-azadispiro[3.1.56.14]dodecane-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: dichloromethane / 0.5 h / 10 °C / Inert atmosphere 2.1: potassium carbonate / tetrahydrofuran; water / 2 h / 10 °C / Inert atmosphere 3.1: Zn-Cu complex / diethyl ether / 2 h / 15 - 30 °C / Inert atmosphere 4.1: acetic acid; zinc / 3 h / 10 - 80 °C / Inert atmosphere 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5.2: 1 h / 0 °C / Inert atmosphere 6.1: ammonium hydroxide; hydrogen / methanol / 6 h / 25 °C / 2585.81 Torr
  • 17
  • [ 1356476-38-4 ]
  • benzyl 2-methylene-7-azaspiro[3.5]nonane-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 0.5 h / 10 °C / Inert atmosphere 2: potassium carbonate / tetrahydrofuran; water / 2 h / 10 °C / Inert atmosphere
  • 18
  • [ 1356476-38-4 ]
  • benzyl 3,3-dichloro-2-oxo-9-azadispiro[3.1.56.14]dodecane-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dichloromethane / 0.5 h / 10 °C / Inert atmosphere 2: potassium carbonate / tetrahydrofuran; water / 2 h / 10 °C / Inert atmosphere 3: Zn-Cu complex / diethyl ether / 2 h / 15 - 30 °C / Inert atmosphere
  • 19
  • [ 1356476-38-4 ]
  • benzyl 2-oxo-9-azadispiro[3.1.56.14]dodecane-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dichloromethane / 0.5 h / 10 °C / Inert atmosphere 2: potassium carbonate / tetrahydrofuran; water / 2 h / 10 °C / Inert atmosphere 3: Zn-Cu complex / diethyl ether / 2 h / 15 - 30 °C / Inert atmosphere 4: acetic acid; zinc / 3 h / 10 - 80 °C / Inert atmosphere
  • 20
  • [ 1356476-38-4 ]
  • benzyl 2-(cyanomethylene)-9-azadispiro[3.1.56.14]dodecane-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: dichloromethane / 0.5 h / 10 °C / Inert atmosphere 2.1: potassium carbonate / tetrahydrofuran; water / 2 h / 10 °C / Inert atmosphere 3.1: Zn-Cu complex / diethyl ether / 2 h / 15 - 30 °C / Inert atmosphere 4.1: acetic acid; zinc / 3 h / 10 - 80 °C / Inert atmosphere 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5.2: 1 h / 0 °C / Inert atmosphere
  • 21
  • [ 1356476-38-4 ]
  • 4-[2-(9-azadispiro[3.1.56.14]dodecan-2-yl)ethylamino]-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione hydrobromide salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: dichloromethane / 0.5 h / 10 °C / Inert atmosphere 2.1: potassium carbonate / tetrahydrofuran; water / 2 h / 10 °C / Inert atmosphere 3.1: Zn-Cu complex / diethyl ether / 2 h / 15 - 30 °C / Inert atmosphere 4.1: acetic acid; zinc / 3 h / 10 - 80 °C / Inert atmosphere 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5.2: 1 h / 0 °C / Inert atmosphere 6.1: ammonium hydroxide; hydrogen / methanol / 6 h / 25 °C / 2585.81 Torr 7.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 2 h / 130 °C / Inert atmosphere 8.1: acetic acid; hydrogen bromide / dichloromethane / 1 h / 20 °C / Inert atmosphere
  • 22
  • [ 1356476-38-4 ]
  • benzyl 2-[2-[[2-(2,6-dioxo-3-piperidyl)-1,3-dioxoisoindolin-4-yl]amino]ethyl]-9-azadispiro[3.1.56.14]dodecane-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: dichloromethane / 0.5 h / 10 °C / Inert atmosphere 2.1: potassium carbonate / tetrahydrofuran; water / 2 h / 10 °C / Inert atmosphere 3.1: Zn-Cu complex / diethyl ether / 2 h / 15 - 30 °C / Inert atmosphere 4.1: acetic acid; zinc / 3 h / 10 - 80 °C / Inert atmosphere 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5.2: 1 h / 0 °C / Inert atmosphere 6.1: ammonium hydroxide; hydrogen / methanol / 6 h / 25 °C / 2585.81 Torr 7.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 2 h / 130 °C / Inert atmosphere
  • 23
  • [ 1356476-38-4 ]
  • C50H56F3N7O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: dichloromethane / 0.5 h / 10 °C / Inert atmosphere 2.1: potassium carbonate / tetrahydrofuran; water / 2 h / 10 °C / Inert atmosphere 3.1: Zn-Cu complex / diethyl ether / 2 h / 15 - 30 °C / Inert atmosphere 4.1: acetic acid; zinc / 3 h / 10 - 80 °C / Inert atmosphere 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5.2: 1 h / 0 °C / Inert atmosphere 6.1: ammonium hydroxide; hydrogen / methanol / 6 h / 25 °C / 2585.81 Torr 7.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 2 h / 130 °C / Inert atmosphere 8.1: acetic acid; hydrogen bromide / dichloromethane / 1 h / 20 °C / Inert atmosphere 9.1: triethylamine / tetrahydrofuran / 0.17 h / 25 °C / Inert atmosphere 9.2: 0.33 h / 25 °C / Inert atmosphere 9.3: 2 h / 0 - 25 °C / Inert atmosphere
  • 24
  • [ 1356476-38-4 ]
  • [ 76-05-1 ]
  • C9H15N*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In dichloromethane at 10℃; for 0.5h; Inert atmosphere; Step 2 - 2-Methylene-7-azaspirol3.51nonane To a solution of tert-butyl 2-methylene-7-azaspiro[3.5]nonane-7-carboxylate (8.80 g, 37.0 mmol) in DCM (50 mL) was added TFA (30.8 g, 270 mmol, 20 mL). The reaction mixture was stirred at 10 °C for 0.5 hr. On completion, the reaction mixture was concentrated in vacuo to give the title compound (9.00 g, 96% yield, TFA salt) as yellow oil. NMR (400 MHz, CDCF) 5 7.82 (br s, 2H), 4.97 - 4.89 (m, 2H), 3.19 (s, 4H), 2.54 (t, J= 2.4 Hz, 4H), 1.97 - 1.86 (m, 4H).
  • 25
  • [ 1356476-38-4 ]
  • [ 1356476-27-1 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: tert-butyl 2-methylene-7-azaspiro[3.5]nonane-7-carboxylate With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 70℃; for 6h; Inert atmosphere; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0 - 25℃; for 12h; Inert atmosphere; B Step B. Tert-butyl 2-(hydroxymethyl)-7-azaspiro[3.5]nonan-7-carboxylate Under N2, 9-BBN (15 mL, 7.5 mmol) was added to a solution of tert-butyl 2-methylene-7-azaspiro[3.5]nonan-7-carboxylate (1.2 g, 5.06 mmol) in THF (20 mL). After the mixture was stirred at 70° C. for 6 h, the reaction was cooled to 0° C. and NaOH (3 N, 8 mL) and H2O2 (8 mL) were added. The reaction mixture was stirred at 25° C. for 12 h. After completion of the reaction, the reaction mixture was quenched with ice water (20 mL) and extracted with DCM (3*50 mL). The combined organic layers were dried over Na2SO4 and concentrated under vacuum to obtain a residue. The residue was purified by column chromatography on silica gel eluted with ethyl acetate (70%) in petroleum ether to obtain the title compound (1 g, 78%). 1H NMR (400 MHz, DMSO-d6) δ 4.44 (t, J=5.2 Hz, 1H), 3.35 (s, 2H), 3.24 (s, 2H), 3.15 (s, 2H), 2.36-2.24 (m, 1H), 1.76 (t, J=10.4 Hz, 2H), 1.50-1.40 (m, 4H), 1.41-1.30 (m, 11H) ppm.
78 % Stage #1: tert-butyl 2-methylene-7-azaspiro[3.5]nonane-7-carboxylate With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 70℃; Inert atmosphere; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0 - 25℃; Inert atmosphere; B Step B. Tert-butyl 2-(hydroxymethyl)-7-azaspiro[3.5]nonan-7-carboxylate Under N2, 9-BBN (15 mL, 7.5 mmol) was added to a solution of tert-butyl 2-methylene-7-azaspiro[3.5]nonan-7-carboxylate (1.2 g, 5.06 mmol) in THF (20 mL). After the mixture was stirred at 70° C. for 6 h, the reaction was cooled to 0° C. and NaOH (3 N, 8 mL) and H2O2 (8 mL) were added. The reaction mixture was stirred at 25° C. for 12 h. After completion of the reaction, the reaction mixture was quenched with ice water (20 mL) and extracted with DCM (3*50 mL). The combined organic layers were dried over Na2SO4 and concentrated under vacuum to obtain a residue. The residue was purified by column chromatography on silica gel eluted with ethyl acetate (70%) in petroleum ether to obtain the title compound (1 g, 78%). 1H NMR (400 MHz, DMSO-d6) δ 4.44 (t, J=5.2 Hz, 1H), 3.35 (s, 2H), 3.24 (s, 2H), 3.15 (s, 2H), 2.36-2.24 (m, 1H), 1.76 (t, J=10.4 Hz, 2H), 1.50-1.40 (m, 4H), 1.41-1.30 (m, 11H) ppm.
78 % Stage #1: tert-butyl 2-methylene-7-azaspiro[3.5]nonane-7-carboxylate With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 70℃; Inert atmosphere; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0 - 25℃; Inert atmosphere; B Step B. Tert-butyl 2-(hydroxymethyl)-7-azaspiro[3.5]nonan-7-carboxylate Under N2, 9-BBN (15 mL, 7.5 mmol) was added to a solution of tert-butyl 2-methylene-7-azaspiro[3.5]nonan-7-carboxylate (1.2 g, 5.06 mmol) in THF (20 mL). After the mixture was stirred at 70° C. for 6 h, the reaction was cooled to 0° C. and NaOH (3 N, 8 mL) and H2O2 (8 mL) were added. The reaction mixture was stirred at 25° C. for 12 h. After completion of the reaction, the reaction mixture was quenched with ice water (20 mL) and extracted with DCM (3*50 mL). The combined organic layers were dried over Na2SO4 and concentrated under vacuum to obtain a residue. The residue was purified by column chromatography on silica gel eluted with ethyl acetate (70%) in petroleum ether to obtain the title compound (1 g, 78%). 1H NMR (400 MHz, DMSO-d6) δ 4.44 (t, J=5.2 Hz, 1H), 3.35 (s, 2H), 3.24 (s, 2H), 3.15 (s, 2H), 2.36-2.24 (m, 1H), 1.76 (t, J=10.4 Hz, 2H), 1.50-1.40 (m, 4H), 1.41-1.30 (m, 11H) ppm.
78 % With dihydrogen peroxide In Petroleum ether B Step B. Step B. Tert-butyl 2-(hydroxymethyl)-7-azaspiro[3.5]nonan-7-carboxylate Under N2, 9-BBN (15 mL, 7.5 mmol) was added to a solution of tert-butyl 2-methylene-7-azaspiro[3.5]nonan-7-carboxylate (1.2 g, 5.06 mmol) in THF (20 mL). After the mixture was stirred at 70° C. for 6 h, the reaction was cooled to 0° C. and NaOH (3 N, 8 mL) and H2O2 (8 mL) were added. The reaction mixture was stirred at 25° C. for 12 h. After completion of the reaction, the reaction mixture was quenched with ice water (20 mL) and extracted with DCM (3*50 mL). The combined organic layers were dried over Na2SO4 and concentrated under vacuum to obtain a residue. The residue was purified by column chromatography on silica gel eluted with ethyl acetate (70%) in petroleum ether to obtain the title compound (1 g, 78%). 1H NMR (400 MHz, DMSO-d6) δ 4.44 (t, J=5.2 Hz, 1H), 3.35 (s, 2H), 3.24 (s, 2H), 3.15 (s, 2H), 2.36-2.24 (m, 1H), 1.76 (t, J=10.4 Hz, 2H), 1.50-1.40 (m, 4H), 1.41-1.30 (m, 11H) ppm.

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