CAS No.866783-12-2,(S)-(4,5-diMethoxy-1,2-dihydrocyclobutabenzen-1-yl)-N-MethylMethanaMine Suppliers

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Basic Information

Molecular Structure:
CAS No.:	866783-12-2
Name:	(S)-(4,5-diMethoxy-1,2-dihydrocyclobutabenzen-1-yl)-N-MethylMethanaMine
Article Data:	8

Formula:	C12H17NO2
Molecular Weight:	207.272
Synonyms:	(1S)-4,5-Dimethoxy-1-(Methylaminoethyl)Benzocyclobutane;(S)-(4,5-diMethoxy-1,2-dihydrocyclobutabenzen-1-yl)-N-MethylMethanaMine;(S)-1-(3,4-DiMethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)-N-MethylMethanaMine;1-[(7S)-3,4-dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl]-N-methylmethanamine
PSA:	30.49000
LogP:	1.95380

Synthetic route

: (1S)-4,5-dimethoxy-1-[(methylamino)methyl]benzocyclobutane N-acetyl-L-glutamic acid

: 866783-12-2
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; dichloromethane; water at 20℃; for 1h; pH=10 - 11;	99%

: (1S)-4,5-dimethoxy-1-[(methylamino)methyl]benzocyclobutane dextro mandelate

: 866783-12-2
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 20℃; for 1h; pH=10 - 11;	96%

: 869856-10-0
ethyl {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}carbamate

: 866783-12-2
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine

Conditions

Conditions	Yield
Stage #1: ethyl {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}carbamate With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1h; Heating / reflux; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 15℃;	93%

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

: 866783-12-2
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine

Conditions

Conditions	Yield
Stage #1: (7S)-3,4-dimethoxy-N-methylbicyclo[4.2.0]octa-1,3,5-triene-7-carboxamide With sodium tetrahydroborate; iodine In tetrahydrofuran for 24h; Reflux; Stage #2: With hydrogenchloride; water pH=3;	90%
With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Reflux;	46%

: N-[[3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl]-N-methylamine (S)-mandelate

: 866783-12-2
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine

Conditions

Conditions	Yield
With sodium hydroxide In water; ethyl acetate at 25℃; for 0.166667h;	n/a

: C12H17NO2*C20H18O8

: 866783-12-2
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine

Conditions

Conditions	Yield
With sodium hydroxide In water

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

: 866783-12-2
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium hydroxide / ethanol / 5 h / Reflux 2.1: (R)-1-phenyl-ethyl-amine / isopropyl alcohol / 1 h / Reflux; Resolution of racemate 3.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 20 °C 4.1: iodine; sodium tetrahydroborate / tetrahydrofuran / 24 h / Reflux 4.2: pH 3 View Scheme
Multi-step reaction with 5 steps 1.1: borane-THF / tetrahydrofuran / 12 h / 20 °C 1.2: 1 h 2.1: triethylamine / dichloromethane / 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / Reflux 4.1: ethanol / Resolution of racemate 5.1: sodium hydroxide / ethyl acetate View Scheme
Multi-step reaction with 3 steps 1.1: nitrilase of Rhodococcus erythropolis NCIMB11215 / aq. phosphate buffer; dimethyl sulfoxide / 96 h / 30 °C / pH 7.3 / Enzymatic reaction 2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 20 °C 2.2: 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / Reflux View Scheme

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

: 866783-12-2
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: (R)-1-phenyl-ethyl-amine / isopropyl alcohol / 1 h / Reflux; Resolution of racemate 2.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 20 °C 3.1: iodine; sodium tetrahydroborate / tetrahydrofuran / 24 h / Reflux 3.2: pH 3 View Scheme

: 53207-00-4
1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene

: 866783-12-2
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: n-butyllithium / tetrahydrofuran; cyclohexane / 0.25 h / -60 °C 1.2: 1 h 2.1: sodium amide / 2 h / 20 °C 3.1: borane-THF / tetrahydrofuran / 12 h / 20 °C 3.2: 1 h 4.1: triethylamine / dichloromethane / 20 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / Reflux 6.1: ethanol / Resolution of racemate 7.1: sodium hydroxide / ethyl acetate View Scheme

Yield

Multi-step reaction with 7 steps
1.1: n-butyllithium / tetrahydrofuran; cyclohexane / 0.25 h / -60 °C
1.2: 1 h
2.1: sodium amide / 2 h / 20 °C
3.1: borane-THF / tetrahydrofuran / 12 h / 20 °C
3.2: 1 h
4.1: triethylamine / dichloromethane / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / Reflux
6.1: ethanol / Resolution of racemate
7.1: sodium hydroxide / ethyl acetate
View Scheme

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

: 866783-12-2
[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: sodium amide / 2 h / 20 °C 2.1: borane-THF / tetrahydrofuran / 12 h / 20 °C 2.2: 1 h 3.1: triethylamine / dichloromethane / 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / Reflux 5.1: ethanol / Resolution of racemate 6.1: sodium hydroxide / ethyl acetate View Scheme