CAS No.41234-23-5,4,5-Dimethoxybenzocyclobutene-1-carboxylic acid Suppliers

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4,5-Dimethoxybenzocyclobutene-1-carboxylic acid

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Siwei Development Group Ltd.

Product name: 4,5-Dimethoxybenzocyclobutene-1-Carboxylic Acid CAS No.：41234-23-5 Molecule Formula：C11H12O4 Molecule Weight：208.21 Purity: 98.0% Package: 25kg/drum Description：White powder Manufacture Standards：Enterprise Standard

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3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid cas no. 41234-23-5 98%

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Propanenitrile,2-[[2-[(2-aminoethyl)amino]ethyl]amino]-

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3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid41234-23-5

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4,5-dimethoxy-1,2-dihydrocyclobuta benzene-1-carboxylic acid

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4,5-Dimethoxybenzocyclobutane-1-carboxylic acid

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Synthetic route

: 35202-54-1
3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 5h; Reflux;	95%
Stage #1: 3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile With water; potassium hydroxide for 4h; Reflux; Stage #2: With hydrogenchloride In water at 20℃;	94%
With over-expressed nitrilase of Rhodococcus rhodochrous NCIMB 11216 In aq. phosphate buffer; ethanol at 30℃; for 2h; pH=7; Enzymatic reaction;	100 %Chromat.

: 1220993-48-5
(R)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: (R)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid With potassium hydroxide In water for 4h; Stage #2: With hydrogenchloride In water for 0.5h; Cooling with ice-water bath;	94%
With sodium ethanolate In ethanol for 18h; Reflux;
With acetic acid at 80 - 100℃; Reagent/catalyst;	56 g

: 1069115-32-7
dimethyl 4,5-dimethoxycyclobutabenzene-1,1(2H)-dicarboxylate

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: dimethyl 4,5-dimethoxycyclobutabenzene-1,1(2H)-dicarboxylate With potassium cyanide In dimethyl sulfoxide at 130℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride; water In diethyl ether; dimethyl sulfoxide at 20℃; for 1h;

: 3,4-dimethoxy-bicyclo[4.2.0]octa-1.3,5-triene-7-carboxylic acid (S)-(-)-1-(naphthyl)-ethylamine

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / dichloromethane; water / 0.33 h 2.1: potassium hydroxide / water / 4 h 2.2: 0.5 h / Cooling with ice-water bath View Scheme

: 3,4-dimethoxy-bicyclo[4.2.0]octa-1.3,5-triene-7-carboxylic acid cinchonidine

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3 2.1: potassium hydroxide / water / 4 h 2.2: 0.5 h / Cooling with ice-water bath View Scheme

: 3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid (+)-cinchonine

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water 2.1: potassium hydroxide / water / 4 h 2.2: 0.5 h / Cooling with ice-water bath View Scheme

: 35249-62-8
3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / -10 °C / Inert atmosphere 2.1: potassium hydroxide; water / 4 h / Reflux 2.2: 20 °C View Scheme

: 1214788-46-1
(R)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)nitrile

A: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

B: 55171-70-5
3,4-Dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid amide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / isopropyl alcohol / 2 h / 65 °C 2: nitrilase NIT 115 / aq. phosphate buffer; dimethyl sulfoxide / 72 h / 28 °C / pH 7 / Enzymatic reaction View Scheme

: 1214788-46-1
(R)-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)nitrile

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / isopropyl alcohol / 2 h / 65 °C 2: over-expressed nitrilase of Rhodococcus rhodochrous NCIMB 11216 / ethanol; aq. phosphate buffer / 2 h / 30 °C / pH 7 / Enzymatic reaction View Scheme

: 35202-54-1
3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

A: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

B: 55171-70-5
3,4-Dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid amide

Conditions

Conditions	Yield
With nitrilase NIT 110 In aq. phosphate buffer; dimethyl sulfoxide at 28℃; for 72h; pH=7; Reagent/catalyst; Enzymatic reaction;	A 15 %Chromat. B 24 %Chromat.
With nitrilase NIT 115 In aq. phosphate buffer; dimethyl sulfoxide at 28℃; for 72h; pH=7; Enzymatic reaction;	A 47 %Chromat. B 7 %Chromat.

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

A: 1220993-48-5
(R)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

B: 1220993-44-1
(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid

Conditions

Conditions	Yield
Stage #1: (R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid With (R)-1-phenyl-ethyl-amine In isopropyl alcohol for 1h; Reflux; Resolution of racemate; Stage #2: With hydrogenchloride; water Reagent/catalyst; Solvent; Time;	A n/a B 76.8%
Multi-step reaction with 2 steps 1: ethyl acetate / 1 h / 18 °C / Heating 2: hydrogenchloride / dichloromethane; water / 0.33 h View Scheme
Multi-step reaction with 2 steps 1: acetone / 0.5 h / Reflux; Cooling 2: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3 View Scheme

: 3886-70-2
(R)-1-(1-Naphthyl)ethylamine

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

A: 3,4-dimethoxy-bicyclo[4.2.0]octa-1.3,5-triene-7-carboxylic acid (R)-(-)-1-(naphthyl)-ethylamine

B: (S)-3,4-dimethoxy-bicyclo[4.2.0]octa-1.3,5-triene-7-carboxylic acid (R)-(-)-1-(naphthyl)-ethylamine

Conditions

Conditions	Yield
In ethyl acetate Heating;	A n/a B 46%

...Expand

: 2627-86-3
(S)-1-phenyl-ethylamine

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

A: 1220993-48-5
(R)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

B: C11H12O4*C8H11N

Conditions

Conditions	Yield
In ethanol; 1,2-dichloro-ethane at 35℃; Solvent; Temperature; Reflux;	A n/a B 41.3%

...Expand

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 343779-04-4
3,4-Dimethoxy-bicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonyl chloride

Conditions

Conditions	Yield
With oxalyl dichloride In benzene for 2h; Ambient temperature;

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 73344-68-0
N-(3-butenyl)-4,5-dimethyoxybenzocyclobutenylmethylamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: oxalyl chloride / benzene / 2 h / Ambient temperature 2: pyridine / CH2Cl2 / 1 h / Ambient temperature 3: LiAlH4, AlCl3 / diethyl ether / 2 h View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 73344-66-8
N-(3-butenyl)-4,5-dimethoxybenzocyclobutene 1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl chloride / benzene / 2 h / Ambient temperature 2: pyridine / CH2Cl2 / 1 h / Ambient temperature View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 73344-71-5, 73344-77-1
cis-8,9-dimethoxy-1,2,3,4,4a,5,6,10b-octahydrobenzisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: oxalyl chloride / benzene / 2 h / Ambient temperature 2: pyridine / CH2Cl2 / 1 h / Ambient temperature 3: LiAlH4, AlCl3 / diethyl ether / 2 h 4: various solvent(s) / 18 h / Heating View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 73344-71-5, 73344-77-1
trans-8,9-dimethoxy-1,2,3,4,4a,5,6,10b-octahydrobenzisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: oxalyl chloride / benzene / 2 h / Ambient temperature 2: pyridine / CH2Cl2 / 1 h / Ambient temperature 3: LiAlH4, AlCl3 / diethyl ether / 2 h 4: various solvent(s) / 18 h / Heating View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: trans-N-methyl-8,9-dimethoxy-1,2,3,4,4a,5,6,10b-octahydrobenzisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: oxalyl chloride / benzene / 2 h / Ambient temperature 2: pyridine / CH2Cl2 / 1 h / Ambient temperature 3: LiAlH4, AlCl3 / diethyl ether / 2 h 4: various solvent(s) / 18 h / Heating 5: NaCNBH3, acetic acid / methanol; H2O View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: trans-N-ethyl-8,9-dimethoxy-1,2,3,4,4a,5,6,10b-octahydrobenzisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: oxalyl chloride / benzene / 2 h / Ambient temperature 2: pyridine / CH2Cl2 / 1 h / Ambient temperature 3: LiAlH4, AlCl3 / diethyl ether / 2 h 4: various solvent(s) / 18 h / Heating 5: NaBH4 / benzene View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: cis-N-n-propyl-8,9-dimethoxy-1,2,3,4,4a,5,6,10b-octahydrobenzisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: oxalyl chloride / benzene / 2 h / Ambient temperature 2: pyridine / CH2Cl2 / 1 h / Ambient temperature 3: LiAlH4, AlCl3 / diethyl ether / 2 h 4: various solvent(s) / 18 h / Heating 5: NaBH4 / benzene View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: trans-N-n-propyl-8,9-dimethoxy-1,2,3,4,4a,5,6,10b-octahydrobenzisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: oxalyl chloride / benzene / 2 h / Ambient temperature 2: pyridine / CH2Cl2 / 1 h / Ambient temperature 3: LiAlH4, AlCl3 / diethyl ether / 2 h 4: various solvent(s) / 18 h / Heating 5: NaBH4 / benzene View Scheme

: 67-56-1
methanol

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 1206230-25-2
Methyl (R,S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylate

Conditions

Conditions	Yield
With sulfuric acid for 2h; Reflux;

: 10420-89-0
(S)-1-(1-Naphthyl)ethylamine

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

A: 3,4-dimethoxy-bicyclo[4.2.0]octa-1.3,5-triene-7-carboxylic acid (S)-(-)-1-(naphthyl)-ethylamine

B: 1346558-07-3
(S)-3,4-dimethoxy-bicyclo[4.2.0]octa-1.3,5-triene-7-carboxylic acid (S)-(-)-1-(naphthyl)-ethylamine

Conditions

Conditions	Yield
In ethyl acetate at 18℃; for 1h; Heating;	A n/a B n/a

...Expand

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 118-10-5, 485-70-1, 485-71-2, 550-54-9, 40134-63-2, 72402-55-2, 72402-56-3
cinchonine

A: 3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid (+)-cinchonine

B: (S)-3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid (+)-cinchonine

Conditions

Conditions	Yield
In ethyl acetate at 0℃; for 1.25h; Reflux;	A n/a B n/a

...Expand

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 118-10-5, 485-70-1, 485-71-2, 550-54-9, 40134-63-2, 72402-55-2, 72402-56-3
cinchonidine

A: 3,4-dimethoxy-bicyclo[4.2.0]octa-1.3,5-triene-7-carboxylic acid cinchonidine

B: 1346558-10-8
(R)-3,4-dimethoxy-bicyclo[4.2.0]octa-1.3,5-triene-7-carboxylic acid cinchonidine

Conditions

Conditions	Yield
In acetone for 0.5h; Reflux; Cooling;

...Expand

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 866783-13-3
1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: ethyl acetate / 1.25 h / 0 °C / Reflux 2.1: hydrogenchloride / dichloromethane; water / 0.08 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: ethyl acetate / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: acetone / 0.5 h / Reflux; Cooling 2.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 148849-67-6
ivabradine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: ethyl acetate / 1.25 h / 0 °C / Reflux 2.1: hydrogenchloride / dichloromethane; water / 0.08 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 8 steps 1.1: acetone / 0.5 h / Reflux; Cooling 2.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 8 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 8 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme
Multi-step reaction with 8 steps 1.1: ethyl acetate / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / water / 6 h / 45 °C / 7500.75 Torr View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 1086026-31-4
3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: ethyl acetate / 1.25 h / 0 °C / Reflux 2.1: hydrogenchloride / dichloromethane; water / 0.08 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere View Scheme
Multi-step reaction with 7 steps 1.1: acetone / 0.5 h / Reflux; Cooling 2.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere View Scheme
Multi-step reaction with 7 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere View Scheme
Multi-step reaction with 7 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere View Scheme
Multi-step reaction with 7 steps 1.1: ethyl acetate / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 1220993-44-1
(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl acetate / 1.25 h / 0 °C / Reflux 2: hydrogenchloride / dichloromethane; water / 0.08 h View Scheme
Multi-step reaction with 2 steps 1: ethyl acetate / 1 h / 18 °C / Heating 2: hydrogenchloride / dichloromethane; water / 0.33 h View Scheme
Multi-step reaction with 2 steps 1: ethyl acetate / Heating 2: hydrogenchloride / dichloromethane; water / 0.33 h View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 1220993-48-5
(R)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl acetate / 1.25 h / 0 °C / Reflux 2: hydrogenchloride / water View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 1220993-43-0
(7S)-3,4-dimethoxy-N-methylbicyclo[4.2.0]octa-1,3,5-triene-7-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: ethyl acetate / 1.25 h / 0 °C / Reflux 2: hydrogenchloride / dichloromethane; water / 0.08 h 3: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4: dichloromethane; water / 0 - 10 °C View Scheme
Multi-step reaction with 4 steps 1: ethyl acetate / 1 h / 18 °C / Heating 2: hydrogenchloride / dichloromethane; water / 0.33 h 3: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4: dichloromethane; water / 0 - 10 °C View Scheme
Multi-step reaction with 4 steps 1: ethyl acetate / 1 h / 18 °C / Heating 2: hydrogenchloride / dichloromethane; water / 0.33 h 3: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4: dichloromethane; water / 0 - 10 °C View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 1220993-45-2
(S)-3,4-dimethoxy-bicyclo[4.2.0]octa-1.3,5-triene-7-carboxylic acid chloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethyl acetate / 1.25 h / 0 °C / Reflux 2: hydrogenchloride / dichloromethane; water / 0.08 h 3: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C View Scheme
Multi-step reaction with 3 steps 1: ethyl acetate / 1 h / 18 °C / Heating 2: hydrogenchloride / dichloromethane; water / 0.33 h 3: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C View Scheme
Multi-step reaction with 3 steps 1: ethyl acetate / 1 h / 18 °C / Heating 2: hydrogenchloride / dichloromethane; water / 0.33 h 3: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 1346558-08-4
dehydro-ivabradine oxalate

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: ethyl acetate / 1.25 h / 0 °C / Reflux 2.1: hydrogenchloride / dichloromethane; water / 0.08 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: acetone / 0.5 h / Reflux; Cooling 2.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: ethyl acetate / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C View Scheme

: 41234-23-5
(R,S)-4,5-dimethoxy-1,2-dihydrocyclobutabenzene-1-carboxylic acid

: 1346558-09-5
3-{3-[((S)-3,4-dimethoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-ylmethyl)-methyl-amino]-propyl}-7,8-dimethoxy-1,3-dihydro-benzo[d]azepine-2-one nitrate

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: ethyl acetate / 1.25 h / 0 °C / Reflux 2.1: hydrogenchloride / dichloromethane; water / 0.08 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: nitric acid / ethanol; water View Scheme
Multi-step reaction with 8 steps 1.1: acetone / 0.5 h / Reflux; Cooling 2.1: hydrogenchloride / ethyl acetate; water / 0.08 h / pH 3 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: nitric acid / ethanol; water View Scheme
Multi-step reaction with 8 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: nitric acid / ethanol; water View Scheme
Multi-step reaction with 8 steps 1.1: ethyl acetate / 1 h / 18 °C / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: nitric acid / ethanol; water View Scheme
Multi-step reaction with 8 steps 1.1: ethyl acetate / Heating 2.1: hydrogenchloride / dichloromethane; water / 0.33 h 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 15 - 25 °C 4.1: dichloromethane; water / 0 - 10 °C 5.1: borane-THF / tetrahydrofuran / 20 - 50 °C 5.2: 0.25 h / 0 - 5 °C 5.3: 2.5 h / 0 °C / Reflux 6.1: potassium carbonate; sodium iodide / 1-methyl-pyrrolidin-2-one / 20 - 60 °C / Inert atmosphere 6.2: 2 h / 20 °C 7.1: potassium carbonate / water / 0.08 h 7.2: Inert atmosphere 8.1: nitric acid / ethanol; water View Scheme

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