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[ CAS No. 1171197-20-8 ] {[proInfo.proName]}

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Chemical Structure| 1171197-20-8
Chemical Structure| 1171197-20-8
Structure of 1171197-20-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1171197-20-8 ]

CAS No. :1171197-20-8 MDL No. :MFCD27921195
Formula : C16H24N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 276.37 Pubchem ID :-
Synonyms :

Safety of [ 1171197-20-8 ]

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
GHS Pictogram:

Application In Synthesis of [ 1171197-20-8 ]

* 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 [ 1171197-20-8 ]

[ 1171197-20-8 ] Synthesis Path-Downstream   1~39

  • 2
  • [ 138229-59-1 ]
  • [ 1171197-20-8 ]
  • [ 1038916-05-0 ]
  • 3
  • [ 875798-79-1 ]
  • [ 1171197-20-8 ]
  • [ 1263284-59-8 ]
YieldReaction ConditionsOperation in experiment
With Chiralpak AD In ethanol; n-heptane Resolution of racemate; 150.a Example 150 3,4-Dichloro-N-((R)-4-piperidin-3-yl-phenyl)-benzamide hydrochloride(a) (R)-tert-Butyl 3 -(4-aminophenyl)piperidine-l -carboxylate & (S)-tert-Butyl 3-(4- aminophenyDpiperidine- 1 -carboxylate The enantiomers of (RS)-tert-butyl 3-(4-aminophenyl)piperidine-l -carboxylate (6.00 g, CAS 875798-79-1) were separated using chiral HPLC (column: Chiralpak AD, 5 x 50 cm; eluent: 10 % ethanol/heptane; pressure: 15 bar; flow rate: 35 ml/min) affording: (+)-(R)-tert-Butyl 3-(4-aminophenyl)piperidine- 1 -carboxylate (2.72 g, white solid)Retention time = 62 min (-)-(Sytert-Butyl 3-(4-aminophenyl)piperidine- 1 -carboxylate (2.65 g, white solid)Retention time = 88 min
With Chiralpak AD In ethanol; n-heptane Resolution of racemate; 150.a The enantiomers of (RS)-tert-butyl 3-(4-aminophenyl)piperidine-1-carboxylate (6.00 g, CAS 875798-79-1) were separated using chiral HPLC (column: Chiralpak AD, 5×50 cm; eluent: 10% ethanol/heptane; pressure: 15 bar; flow rate: 35 ml/min) affording:(+)-(R)-tert-Butyl 3-(4-aminophenyl)piperidine-1-carboxylate (2.72 g, white solid) Retention time=62 min (-)-(S)-tert-Butyl 3-(4-aminophenyl)piperidine-1-carboxylate (2.65 g, white solid) Retention time=88 min
With Chiralpak AD In ethanol; n-heptane Resolution of racemate; Large scale reaction;
  • 4
  • [ 1171197-20-8 ]
  • [ 1038915-64-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: ammonia / methanol / 60 °C 4: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 4 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: ammonia / methanol / 60 °C 4: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 4 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: ammonia / methanol / 60 °C 4: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 4 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: ammonia / methanol / 60 °C 4: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 5 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: ammonia / methanol / 60 °C 5: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 5 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 4: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction 5: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 5 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: ammonia / methanol / 60 °C 5: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 5 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 4: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction 5: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 6 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction 6: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 6 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction 6: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 6 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction 6: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 6 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction 6: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 7 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: water; sodium hydroxide / tetrahydrofuran / 35 °C 5: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 6: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction 7: hydrogenchloride / water; ethyl acetate / 20 °C
Multi-step reaction with 7 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: water; sodium hydroxide / tetrahydrofuran / 35 °C 5: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 6: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction 7: hydrogenchloride / water; ethyl acetate / 20 °C

Reference: [1]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[2]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[3]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[4]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[5]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[6]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[7]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[8]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[9]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[10]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[11]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[12]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[13]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[14]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
  • 5
  • [ 1171197-20-8 ]
  • [ 1196713-67-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction
Multi-step reaction with 2 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C
Multi-step reaction with 2 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction
Multi-step reaction with 2 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C
Multi-step reaction with 3 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating
Multi-step reaction with 3 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating
Multi-step reaction with 2 steps 1: hexane / 18 h / Reflux 2: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C

Reference: [1]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[2]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[3]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[4]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[5]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[6]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[7]Current Patent Assignee: NANJING NMG ADDS - CN106749180, 2017, A Current Patent Assignee: NANJING NMG ADDS - CN106749181, 2017, A
  • 6
  • [ 1171197-20-8 ]
  • [ 1038916-11-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: ammonia / methanol / 60 °C
Multi-step reaction with 3 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: ammonia / methanol / 60 °C
Multi-step reaction with 3 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: ammonia / methanol / 60 °C
Multi-step reaction with 3 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: ammonia / methanol / 60 °C
Multi-step reaction with 4 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: ammonia / methanol / 60 °C
Multi-step reaction with 4 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 4: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 4 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: ammonia / methanol / 60 °C
Multi-step reaction with 4 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 4: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 5 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 5 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 5 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 5 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 5: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 6 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: water; sodium hydroxide / tetrahydrofuran / 35 °C 5: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 6: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 6 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: water; sodium hydroxide / tetrahydrofuran / 35 °C 5: pyridine / dichloromethane / 0.5 h / 20 - 25 °C 6: ammonium bicarbonate / dichloromethane / 20 h / 20 - 25 °C / Large scale reaction
Multi-step reaction with 2 steps 1: isopropyl alcohol / 74 - 82 °C / Inert atmosphere 2: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 8 h / 120 °C / Inert atmosphere

Reference: [1]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[2]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[3]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[4]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[5]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[6]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[7]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[8]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[9]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[10]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[11]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[12]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[13]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[14]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[15]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - WO2019/36441, 2019, A1
  • 8
  • [ 1171197-20-8 ]
  • [ 1038916-08-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C
Multi-step reaction with 2 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C
Multi-step reaction with 3 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: water; sodium hydroxide / tetrahydrofuran / 35 °C
Multi-step reaction with 3 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: water; sodium hydroxide / tetrahydrofuran / 35 °C
Multi-step reaction with 3 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: water; sodium hydroxide / tetrahydrofuran / 35 °C
Multi-step reaction with 3 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: water; sodium hydroxide / tetrahydrofuran / 35 °C
Multi-step reaction with 4 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: water; sodium hydroxide / tetrahydrofuran / 35 °C
Multi-step reaction with 4 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: water; sodium hydroxide / tetrahydrofuran / 35 °C

Reference: [1]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[2]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[3]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[4]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[5]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[6]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[7]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[8]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
  • 9
  • [ 1171197-20-8 ]
  • C29H35N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: pyridine / dichloromethane / 0.5 h / 20 - 25 °C
Multi-step reaction with 3 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: pyridine / dichloromethane / 0.5 h / 20 - 25 °C
Multi-step reaction with 4 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C
Multi-step reaction with 4 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C
Multi-step reaction with 4 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 20 h / 110 °C / Large scale reaction 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C
Multi-step reaction with 4 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C 3: water; sodium hydroxide / tetrahydrofuran / 35 °C 4: pyridine / dichloromethane / 0.5 h / 20 - 25 °C
Multi-step reaction with 5 steps 1: tert-butyl methyl ether / 60 °C 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: water; sodium hydroxide / tetrahydrofuran / 35 °C 5: pyridine / dichloromethane / 0.5 h / 20 - 25 °C
Multi-step reaction with 5 steps 1: 16 h / Reflux 2: sodium azide / N,N-dimethyl-formamide / 90 °C 3: Heating 4: water; sodium hydroxide / tetrahydrofuran / 35 °C 5: pyridine / dichloromethane / 0.5 h / 20 - 25 °C

Reference: [1]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[2]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[3]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[4]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[5]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[6]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[7]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
[8]Wallace, Debra J.; Baxter, Carl A.; Brands, Karel J. M.; Bremeyer, Nadine; Brewer, Sarah E.; Desmond, Richard; Emerson, Khateeta M.; Foley, Jennifer; Fernandez, Paul; Hu, Weifeng; Keen, Stephen P.; Mullens, Peter; Muzzio, Daniel; Sajonz, Peter; Tan, Lushi; Wilson, Robert D.; Zhou, George; Zhou, Guoyue [Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840]
  • 10
  • [ 138229-59-1 ]
  • [ 1171197-20-8 ]
  • C21H32N2O4 [ No CAS ]
  • [ 1312106-32-3 ]
  • 11
  • [ 138229-59-1 ]
  • [ 1171197-20-8 ]
  • [ 1312106-32-3 ]
YieldReaction ConditionsOperation in experiment
92% In ethanol; at 80℃; for 4h; Weigh compound 3 (2.13g, 10.2mmol) in a 100 mL eggplant-shaped flask, add 0.2M absolute ethanol to dissolve and add compound 4 (3S) -3- (4-aminophenyl) piperidine-1-carboxylic acid tert-butyl Ester (2.76g, 10mmol), stirred at reflux at 80 C for 4 hours, until TLC showed that the reaction was complete (petroleum ether: ethyl acetate = 20: 4), the reaction was cooled, crystallized, and filtered, and the obtained filter cake was recrystallized with methanol , Filtered and dried to obtain compound 5 (3.03 g, 92%) as a white solid, which can be used directly in the next step.
41.2 g In hexane; for 18h;Reflux; Compound 11 (23.0 g, 0.11 mol) and compound 8 (30.4.0 g, 0.11 mol)160 mL of n-hexane was added and heated to reflux temperature, reacted at this temperature for 18 hours,The solid was filtered off and washed with n-hexane and dried under reduced pressure (45 C) to give 41.2 g of a brown solid.
41.2 g In hexane; for 18h;Reflux; To a solution of compound 11 (23.0 g, 0.11 mol) and compound 8 (30.4.0 g, 0.11 mol) in n-hexane160 mL and heated to reflux temperature, reacted at this temperature for 18 hours, the solid was filtered off,Washed with n-hexane and dried under reduced pressure (45 C) to give 41.2 g of a brown solid.
  • 15
  • [ 4282-46-6 ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogenchloride; platinum(IV) oxide; hydrogen / methanol; water / 16 h / 10 - 40 °C / 750.08 - 3000.3 Torr / Inert atmosphere; Large scale reaction 2.1: methanol / 60 °C / Resolution of racemate 2.2: 40 °C 3.1: triethylamine / dichloromethane / 0 °C
Multi-step reaction with 4 steps 1.1: hydrogenchloride; platinum(IV) oxide; hydrogen / methanol; water / 16 h / 10 - 40 °C / 750.08 - 3000.3 Torr / Inert atmosphere; Large scale reaction 2.1: methanol / 60 °C / Resolution of racemate 2.2: 40 °C 3.1: sodium hydroxide / dichloromethane 4.1: ethanol / 1 h / 0 °C
Multi-step reaction with 4 steps 1.1: 10 h / 110 °C 2.1: sodium tetrahydroborate; methanol / 8.5 h / 3 - 20 °C 2.2: 24 h / 9120.61 Torr / Autoclave 3.1: L-Tartaric acid / acetonitrile / 10 °C / Reflux 4.1: sodium hydroxide; triethylamine; dmap / dichloromethane / 8 h / 20 °C
  • 16
  • [ 4282-46-6 ]
  • [ 1171197-20-8 ]
  • [ 1263284-59-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride; platinum(IV) oxide; hydrogen / methanol; water / 16 h / 10 - 40 °C / 750.08 - 3000.3 Torr / Inert atmosphere; Large scale reaction 2: dichloromethane / 0.5 h / 0 - 5 °C / Large scale reaction 3: Chiralpak AD / ethanol; n-heptane / Resolution of racemate; Large scale reaction
  • 18
  • [ 19733-56-3 ]
  • [ 1171197-20-8 ]
  • [ 1263284-59-8 ]
  • 19
  • [ 1692-25-7 ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran / 2 h / 66 °C / Large scale reaction 2.1: hydrogenchloride; platinum(IV) oxide; hydrogen / methanol; water / 16 h / 10 - 40 °C / 750.08 - 3000.3 Torr / Inert atmosphere; Large scale reaction 3.1: methanol / 60 °C / Resolution of racemate 3.2: 40 °C 4.1: triethylamine / dichloromethane / 0 °C
Multi-step reaction with 5 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran / 2 h / 66 °C / Large scale reaction 2.1: hydrogenchloride; platinum(IV) oxide; hydrogen / methanol; water / 16 h / 10 - 40 °C / 750.08 - 3000.3 Torr / Inert atmosphere; Large scale reaction 3.1: methanol / 60 °C / Resolution of racemate 3.2: 40 °C 4.1: sodium hydroxide / dichloromethane 5.1: ethanol / 1 h / 0 °C
  • 20
  • [ 1692-25-7 ]
  • [ 1171197-20-8 ]
  • [ 1263284-59-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran / 2 h / 66 °C / Large scale reaction 2: hydrogenchloride; platinum(IV) oxide; hydrogen / methanol; water / 16 h / 10 - 40 °C / 750.08 - 3000.3 Torr / Inert atmosphere; Large scale reaction 3: dichloromethane / 0.5 h / 0 - 5 °C / Large scale reaction 4: Chiralpak AD / ethanol; n-heptane / Resolution of racemate; Large scale reaction
  • 21
  • [ 586-78-7 ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran / 2 h / 66 °C / Large scale reaction 2.1: hydrogenchloride; platinum(IV) oxide; hydrogen / methanol; water / 16 h / 10 - 40 °C / 750.08 - 3000.3 Torr / Inert atmosphere; Large scale reaction 3.1: methanol / 60 °C / Resolution of racemate 3.2: 40 °C 4.1: triethylamine / dichloromethane / 0 °C
Multi-step reaction with 5 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran / 2 h / 66 °C / Large scale reaction 2.1: hydrogenchloride; platinum(IV) oxide; hydrogen / methanol; water / 16 h / 10 - 40 °C / 750.08 - 3000.3 Torr / Inert atmosphere; Large scale reaction 3.1: methanol / 60 °C / Resolution of racemate 3.2: 40 °C 4.1: sodium hydroxide / dichloromethane 5.1: ethanol / 1 h / 0 °C
  • 22
  • [ 586-78-7 ]
  • [ 1171197-20-8 ]
  • [ 1263284-59-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / tetrahydrofuran / 2 h / 66 °C / Large scale reaction 2: hydrogenchloride; platinum(IV) oxide; hydrogen / methanol; water / 16 h / 10 - 40 °C / 750.08 - 3000.3 Torr / Inert atmosphere; Large scale reaction 3: dichloromethane / 0.5 h / 0 - 5 °C / Large scale reaction 4: Chiralpak AD / ethanol; n-heptane / Resolution of racemate; Large scale reaction
  • 23
  • (3S)-3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester benzenesulfonyl-D-phenylglycine salt [ No CAS ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
95.1% With hydrogenchloride In water; ethyl acetate 5 Example 5 A mixture of 2.30 g of (3S) -3- (4-aminophenyl) piperidine-1-carboxylate p-toluenesulfonyl-D-phenylglycine saltSuspended in 40ml of ethyl acetate / 10mL water, dropping 10% hydrochloric acid for hydrolysis, the reaction is completed after the separation of organic phase,The aqueous phase was extracted with ethyl acetate and concentrated to give a resolving agent. The aqueous phase was adjusted to pH 8-10 with aqueous ammonia and extracted three times with ethyl acetate(3S) -3- (4-aminophenyl) piperidine-1-carboxylate (1.06 g, yield 95.1%, ee value94.50%.
  • 24
  • [ 24424-99-5 ]
  • [ 1196713-21-9 ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane at -5 - 5℃; 4 Example 4 Under ice bath to NIR60 (50 g) in dichloromethane (750 mL) A solution of Boc2O (59.47 g) in dichloromethane (500 mL) was added to the solution. After completion of the reaction, water (500 mL) was added to stir and the temperature was raised to 15-25 °C. The mixture was allowed to stand for separation, and concentrated under reduced pressure (45-50 ° C) until the fraction was significantly reduced (about one volume). 200 mL of isopropanol was added, the nitrogen was replaced, the temperature was raised to 55-60 ° C, and the mixture was stirred for half an hour until it was dissolved, and stirring was continued for 2 hours. Slowly add 400 mL of water, Continue to incubate for 5 hours. Gradually cool down to 0 degrees and continue to stir. Filtered at 0 degrees, The filter cake was washed twice with water/isopropanol (3/1 = V: V). Vacuum drying gave 66.6 g of pink solid NIR70. The yield was 85%, the HPLC purity was 98%, and the ee was 98.4%.
12.1 g With dmap; triethylamine; sodium hydroxide In dichloromethane at 20℃; for 8h; 6 Example 6 A solution of compound 7 (25 g, 0.13 mol) was added 110 mL of acetonitrile,After heating to reflux,L-tartaric acid (15.2 g, 0.104 mol) was added in portions and after refluxing for 2 hours,Slowly down to 10 ° C (1.5 hours)And stirred at this temperature overnight. After filtering off the solid, 85 mL of ethanol was added to the solid,After heating to reflux and stirring for 1 hour,Then down to room temperature crystallization 8 hours, filter out the solid,And dried under reduced pressure (45 ° C) to give 16.4 g of an off-white solid,To the resulting solid was added 50 mL of ethyl acetate,And 30 mL of 0.1 M sodium hydroxide solution was added,After stirring for 20 minutes, the mixture was extracted twice with ethyl acetate (2 * 50 mL)The organic phase was washed once with saturated citric acid (100 mL) and the organic phase was dried over anhydrous sodium sulfate,The organic phase was distilled off to give 8.7 g of a pale yellow oil, 60 mL of dichloromethane was added,Di-tert-butyl dicarbonate (10.8 g, 0.05 mol)Triethylamine (5.70 g, 0.057 mol) was added,DMAP (0.460 g, 3.80 mmol) and reacted at room temperature for 8 hours. The reaction solution was washed with saturated sodium bicarbonate,Dried over anhydrous sodium sulfate and the organic phase was distilled off to give 12.1 g of a pale yellow solid
  • 25
  • 1-benzyl-3-(4-nitrophenyl)pyridinium bromide [ No CAS ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol / 8.5 h / 3 - 20 °C 1.2: 24 h / 9120.61 Torr / Autoclave 2.1: L-Tartaric acid / acetonitrile / 10 °C / Reflux 3.1: sodium hydroxide; triethylamine; dmap / dichloromethane / 8 h / 20 °C
  • 26
  • [ 1171197-20-8 ]
  • [ 1038915-60-4 ]
  • 27
  • [ 875798-79-1 ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
91.3% Stage #1: 3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester With copper(l) iodide; (R)-1,1'-binaphthyl-2,2'-phosphoric acid In water; N,N-dimethyl-formamide at 50 - 75℃; for 2h; Stage #2: With hydrogenchloride; sodium hydroxide In water 1 A process for the preparation of tert-butyl (3S) -3- (4-aminophenyl) piperidine-1-carboxylate comprising the steps of 1) 27.6 g (100 mmol) of tert-butyl 3- (4-aminophenyl) piperidine-1-carboxylate, 38.3 g (110 mmol) of (R) - (-) - binaphthol phosphate, (20 mmol) were added to 150 ml of a mixed solvent consisting of DMF and water in a volume ratio of 5: 1. The mixture was then heated to 75 ° C. for 1 hour. After the reaction was continued, the mixture was stirred and allowed to cool to 50 ° C. Incubated for 1 hour, and then naturally cooled to room temperature, and filtered to obtain a solid compound A.2) hydrolyzing the solid compound A obtained in step 1) in 50 ml of 10% hydrochloric acid solution, adding sodium hydroxide after the completion of the hydrolysis reaction, adjusting the pH value to 10, extracting with ethyl acetate, concentrating, recrystallizing petroleum ether, vacuum The yield of tert-butyl (3S) -3- (4-aminophenyl) piperidine-1-carboxylate was 12.6 g, yield 91.3%, HPLC purity 99.91% by area normalization method, ee value 99.57% HPLC (Column: Chiralpak AD, 5 × 50 cm; eluent: 10% ethanol / heptane; pressure: 15 bar; flow rate: 35 ml / min).
  • 28
  • [ 87-69-4 ]
  • [ 24424-99-5 ]
  • [ 19733-56-3 ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
12.1 g 110 mL of acetonitrile was added to Compound 7 (25 g, 0.13 mol), heated to reflux,L-tartaric acid (15.2 g, 0.104 mol) was added portionwise and after refluxing for 2 hours after addition,Slowly reduced to 10 C (within 1.5 hours) and stirred at this temperature overnight. After filtering off the solids,The solid was added with ethanol 85mL, heated to reflux and stirred for 1 hour,After cooling to room temperature crystallization 8 hours, filtered off the solid,And dried under reduced pressure (45 C) to give 16.4g as an off-white solid,The obtained solid was added with 50 mL of ethyl acetate, and 30 mL of 0.1 M sodium hydroxide solution was added thereto,After stirring for 20 minutes, the mixture was extracted twice with ethyl acetate (2 * 50 mL)The organic phase was washed once with saturated citric acid (100 mL), the organic phase was dried over anhydrous sodium sulfate,The organic phase was evaporated under pressure to give a pale yellow oil 8.7g, dichloromethane was added 60mL,Di-tert-butyl dicarbonate(10.8 g, 0.05 mol). Triethylamine (5.70 g, 0.057 mol) and DMAP (0.460 g, 3.80 mmol) were added and the mixture was reacted at room temperature for 8 hours. The reaction mixture was washed with saturated bicarbonate , Dried over anhydrous sodium sulphate and the organic phase was autoclaved to give 12.1 g of light yellow solid.
  • 29
  • [ 40114-49-6 ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -60 °C / Inert atmosphere 1.2: 8 h / Inert atmosphere; Reflux 2.1: acetonitrile / 10 °C / Reflux 2.2: 0.33 h 2.3: 8 h / 20 °C
  • 30
  • [ 171364-83-3 ]
  • [ 1171197-20-8 ]
  • 31
  • C19H22N2O2 [ No CAS ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 20% palladium hydroxide-activated charcoal; acetic acid; hydrogen / dichloromethane; methanol / 45 - 50 °C / 7500.75 - 11251.1 Torr / Autoclave 2: dichloromethane / -5 - 5 °C
  • 32
  • [ 104-03-0 ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / -5 - 5 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 50 °C 3.1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / -5 - 30 °C / Inert atmosphere 3.2: 1 h / 0 - 5 °C 4.1: 20% palladium hydroxide-activated charcoal; acetic acid; hydrogen / dichloromethane; methanol / 45 - 50 °C / 7500.75 - 11251.1 Torr / Autoclave 5.1: dichloromethane / -5 - 5 °C
Multi-step reaction with 5 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / -5 - 5 °C 2.1: potassium carbonate / acetonitrile / 50 °C 3.1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / -5 - 30 °C / Inert atmosphere 3.2: 1 h / 0 - 5 °C 4.1: 20% palladium hydroxide-activated charcoal; acetic acid; hydrogen / dichloromethane; methanol / 45 - 50 °C / 7500.75 - 11251.1 Torr / Autoclave 5.1: dichloromethane / -5 - 5 °C
  • 33
  • C19H21ClN2O3 [ No CAS ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 50 °C 2.1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / -5 - 30 °C / Inert atmosphere 2.2: 1 h / 0 - 5 °C 3.1: 20% palladium hydroxide-activated charcoal; acetic acid; hydrogen / dichloromethane; methanol / 45 - 50 °C / 7500.75 - 11251.1 Torr / Autoclave 4.1: dichloromethane / -5 - 5 °C
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 50 °C 2.1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / -5 - 30 °C / Inert atmosphere 2.2: 1 h / 0 - 5 °C 3.1: 20% palladium hydroxide-activated charcoal; acetic acid; hydrogen / dichloromethane; methanol / 45 - 50 °C / 7500.75 - 11251.1 Torr / Autoclave 4.1: dichloromethane / -5 - 5 °C
  • 34
  • C19H20N2O3 [ No CAS ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / -5 - 30 °C / Inert atmosphere 1.2: 1 h / 0 - 5 °C 2.1: 20% palladium hydroxide-activated charcoal; acetic acid; hydrogen / dichloromethane; methanol / 45 - 50 °C / 7500.75 - 11251.1 Torr / Autoclave 3.1: dichloromethane / -5 - 5 °C
  • 35
  • [ 1171197-20-8 ]
  • [ 1038915-73-9 ]
  • 36
  • [ 1171197-20-8 ]
  • 3-formyl-2-nitrobenzamide [ No CAS ]
  • [ 1038915-73-9 ]
  • 37
  • [ 1171197-20-8 ]
  • 3-formyl-2-nitrobenzamide [ No CAS ]
  • tert-butyl (E)-3-(4-((3-carbamoyl-2-nitrobenzylidene)amino)phenyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
341 g In isopropyl alcohol at 74 - 82℃; Inert atmosphere; 3A; 3B 3-Formyl-2-nitrobenzamide (Compound 11) (252 g), tert-butyl (S)-3-(4-aminophenyl) piperidine-l-carboxylate (Compound 21, can be prepared according to example 2(Q)) (230 g) and IP A (1020 mL) were charged to a vessel under inert atmosphere and heated to 74-82°C for 4-6 h or until HPLC/TLC analysis indicated completion of reaction. After completion of the reaction, the slurry was cooled to 20-30°C, filtered, washed with IP A (2x 170 mL) and dried under reduced pressure at 55-65°C to afford the title compound (Yield: 341g; HPLC Purity: 98.21%).
  • 38
  • [ 1171197-20-8 ]
  • 3-formyl-2-nitrobenzamide [ No CAS ]
  • [ 1038916-11-8 ]
YieldReaction ConditionsOperation in experiment
2.8 g Stage #1: (3S)-3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester; 3-formyl-2-nitrobenzamide In ethanol for 2h; Inert atmosphere; Reflux; Stage #2: With 2,6-dimethylpyridine In ethanol; N,N-dimethyl-formamide Stage #3: With sodium azide In N,N-dimethyl-formamide at 110℃; for 20h; 3D Example 3 (D): Preparation of tert-butyl (S)-3-(4-(7-carbamoyl-2H-indazol-2-yl) phenyl)piperidine-l-carboxylate (Compound Va) (Compound V, R5 is H and R6 is Boc=Compound 22) 3-Formyl-2-nitrobenzamide (Compound 11) (3.5 g), tert-butyl (S)- 3-(4-aminophenyl) piperidine-l-carboxylate (Compound 21) (4.98 g) and ethanol (30 mL) were charged to a round bottomed flask under inert atmosphere and heated to reflux temperature for 2 h or until HPLC/TLC analysis indicated completion of the reaction. DMF (50 mL) and lutidine (2.5 mL) was added to reaction mass to give a clear solution. Ethanol was distilled off and sodium azide (1.72 g) was added. The reaction mass was heated to 110°C for 20 h or until HPLC/TLC analysis indicated completion of the reaction. The reaction mass was cooled to 25°C, THF (200 mL) was added followed by addition of 25% aq. LiCl solution (100 mL, precooled at 5°C) and the layers were separated. The aqueous layer was re-extracted twice with THF (2x50 mL). The organic layers were combined and washed twice with 25% aq. LiCl solution (30 mL). It was passed through small silica bed using MTBE:DCM (1 : 1) (500 mL). Solvent was removed under vacuum till 1-2 volume was left. Reaction mass was cooled to 0-10°C for 2 h. The solid obtained was filtered and suck dried to afford the titled compound as off-white solid (Yield: 2.8 g; HPLC Purity: 98 %).
  • 39
  • tert-butyl (S)-3-(4-aminophenyl)piperidine-1-carboxylate L-tartaric acid salt [ No CAS ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
0.63 g With sodium carbonate In water; ethyl acetate at 20 - 30℃; 2Q Example 2 (Q): Preparation of tert-butyl (S)-3-(4-aminophenyl) piperidine-l- carboxylate (Compound 21) To a mixture of L-tartaric acid salt of tert-butyl (S)-3-(4- aminophenyl) piperidine-l-carboxylate (L-tartaric acid salt of Compound 20) (104 g) in ethyl acetate (500 mL) and water (500 mL) in a reactor, Na2C03 (32.31 g) was added slowly at 20-30°C and stirred for 1-2 h. Layers were settled separated. The organic layer was washed with water (300 mL). The organic layer was concentrated to afford the titled compound (Yield: 0.63 g; Chiral Purity: >99.96% of Desired S- isomer).
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