Product Name

  • Name

    Tetrabenazine

  • EINECS 200-383-6
  • CAS No. 58-46-8
  • Article Data7
  • CAS DataBase
  • Density 1.127 g/cm3
  • Solubility
  • Melting Point 128-130 °C
  • Formula C19H27NO3
  • Boiling Point 448.941 °C at 760 mmHg
  • Molecular Weight 317.428
  • Flash Point 225.311 °C
  • Transport Information
  • Appearance white to off-white solid
  • Safety 24/25
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 58-46-8 (Tetrabenazine)
  • Hazard Symbols HarmfulXn
  • Synonyms 2H-Benzo[a]quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (3S,11bS)-;(3S,11bS)-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one;
  • PSA 38.77000
  • LogP 3.17600

Synthetic route

methanol
67-56-1

methanol

(+/-)-9,10-dihydroxy-3c-isobutyl-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one
89929-27-1

(+/-)-9,10-dihydroxy-3c-isobutyl-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 25 - 30℃; Mitsunobu Displacement; Large scale;96%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

2-acetyl-N,N,N,4-tetramethyl-1-pentanaminium iodide
1069-62-1

2-acetyl-N,N,N,4-tetramethyl-1-pentanaminium iodide

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Stage #1: 6,7-dimethoxy-3,4-dihydro-isoquinoline; 2-acetyl-N,N,N,4-tetramethyl-1-pentanaminium iodide In ethanol at 80℃;
Stage #2: With sodium hydroxide; water In dichloromethane		75%
6,7-dimethoxy-3,4-dihydro-isoquinoline
3382-18-1

6,7-dimethoxy-3,4-dihydro-isoquinoline

C12H18O3

C12H18O3

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Stage #1: 6,7-dimethoxy-3,4-dihydro-isoquinoline; C12H18O3 In ethanol at 60℃; for 72h; Diels-Alder Cycloaddition; Inert atmosphere;
Stage #2: With morpholine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; ethanol at 20℃; for 3h; Inert atmosphere;		69%
3-isobutyl-9,10-dimethoxy-2-methylene-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline

3-isobutyl-9,10-dimethoxy-2-methylene-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Stage #1: 3-isobutyl-9,10-dimethoxy-2-methylene-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinoline With osmium(VIII) oxide; water In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere;
Stage #2: With sodium periodate; 4-methylmorpholine N-oxide In tetrahydrofuran; water at 0℃; for 5h; Inert atmosphere;		61%
3-isobutyl-9,10-dimethoxy-2-oxo-1,3,4,6,7,11b-tetrahydro-2H-pyrido<2,1-a>isoquinoline-1,3-carboxylic acid diethyl ester

3-isobutyl-9,10-dimethoxy-2-oxo-1,3,4,6,7,11b-tetrahydro-2H-pyrido<2,1-a>isoquinoline-1,3-carboxylic acid diethyl ester

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
With hydrogenchloride
4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl-4-methylbenzenesulfonate
1346909-18-9

4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl-4-methylbenzenesulfonate

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
2.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
3.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
3.2: 5 h / 0 °C / Inert atmosphere
View Scheme
6,7-dimethoxy-2-(4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl)-1,2,3,4-tetrahydroisoquinoline
1346909-10-1

6,7-dimethoxy-2-(4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentyl)-1,2,3,4-tetrahydroisoquinoline

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
2.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
2.2: 5 h / 0 °C / Inert atmosphere
View Scheme
methyl 4-methyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pentanoate
1346909-36-1

methyl 4-methyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pentanoate

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / 0.58 h / -20 - -5 °C / Inert atmosphere
2.1: diethyl ether; hexane / 2 h / -78 - 20 °C / Inert atmosphere
3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
3.2: 0.67 h / Inert atmosphere
4.1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C / Inert atmosphere
5.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / diethyl ether / 0 °C / Inert atmosphere
5.2: 1 h / Inert atmosphere
6.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere
7.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
8.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
9.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
9.2: 5 h / 0 °C / Inert atmosphere
View Scheme
N-methoxy-N,4-dimethyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pentane amide
1346909-38-3

N-methoxy-N,4-dimethyl-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pentane amide

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: diethyl ether; hexane / 2 h / -78 - 20 °C / Inert atmosphere
2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
2.2: 0.67 h / Inert atmosphere
3.1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C / Inert atmosphere
4.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / diethyl ether / 0 °C / Inert atmosphere
4.2: 1 h / Inert atmosphere
5.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere
6.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
7.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
8.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
8.2: 5 h / 0 °C / Inert atmosphere
View Scheme
5-methyl-3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)hexan-2-one
1346909-30-5

5-methyl-3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)hexan-2-one

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
1.2: 0.67 h / Inert atmosphere
2.1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C / Inert atmosphere
3.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / diethyl ether / 0 °C / Inert atmosphere
3.2: 1 h / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere
5.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
6.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
7.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
7.2: 5 h / 0 °C / Inert atmosphere
View Scheme
5-methyl-3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)hex-1-ene-2-yl trifluoromethanesulfonate
1346909-40-7

5-methyl-3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)hex-1-ene-2-yl trifluoromethanesulfonate

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C / Inert atmosphere
2.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / diethyl ether / 0 °C / Inert atmosphere
2.2: 1 h / Inert atmosphere
3.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere
4.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
5.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
6.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
6.2: 5 h / 0 °C / Inert atmosphere
View Scheme
3-(hydroxymethyl)-5-methylhex-1-ene-2-yl trifluoromethanesulfonate
1346909-31-6

3-(hydroxymethyl)-5-methylhex-1-ene-2-yl trifluoromethanesulfonate

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / diethyl ether / 0 °C / Inert atmosphere
1.2: 1 h / Inert atmosphere
2.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere
3.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
4.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
5.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
5.2: 5 h / 0 °C / Inert atmosphere
View Scheme
4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentan-1-ol
1346909-44-1

4-methyl-2-(3-(trimethylsilyl)prop-1-ene-2-yl)pentan-1-ol

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere
2.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
3.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
4.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
4.2: 5 h / 0 °C / Inert atmosphere
View Scheme
rac-2-(hydroxymethyl)-4-methylpentanoic acid methyl ester
403804-65-9

rac-2-(hydroxymethyl)-4-methylpentanoic acid methyl ester

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere
2.1: isopropylmagnesium chloride / tetrahydrofuran / 0.58 h / -20 - -5 °C / Inert atmosphere
3.1: diethyl ether; hexane / 2 h / -78 - 20 °C / Inert atmosphere
4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
4.2: 0.67 h / Inert atmosphere
5.1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C / Inert atmosphere
6.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / diethyl ether / 0 °C / Inert atmosphere
6.2: 1 h / Inert atmosphere
7.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere
8.1: sodium carbonate / N,N-dimethyl-formamide / 30 h / 80 °C / Inert atmosphere
9.1: lithium perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere
10.1: osmium(VIII) oxide; water / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
10.2: 5 h / 0 °C / Inert atmosphere
View Scheme
methyl 2-acetyl-4-methylpentanoate
51756-09-3

methyl 2-acetyl-4-methylpentanoate

C19H27NO3

C19H27NO3

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: toluene-4-sulfonic acid / toluene / 18 h / Reflux; Dean-Stark
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
3.2: 1 h / -78 - 20 °C
4.1: hydrogenchloride / tetrahydrofuran; water / 12 h / 20 °C
5.1: acetic acid / toluene / 15 h / Molecular sieve; Reflux
View Scheme
C11H20O4

C11H20O4

C19H27NO3

C19H27NO3

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
2.2: 1 h / -78 - 20 °C
3.1: hydrogenchloride / tetrahydrofuran; water / 12 h / 20 °C
4.1: acetic acid / toluene / 15 h / Molecular sieve; Reflux
View Scheme
4-methyl-2-(2-methyl-1,3-dioxolan-2-yl)pentan-1-ol

4-methyl-2-(2-methyl-1,3-dioxolan-2-yl)pentan-1-ol

C19H27NO3

C19H27NO3

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
1.2: 1 h / -78 - 20 °C
2.1: hydrogenchloride / tetrahydrofuran; water / 12 h / 20 °C
3.1: acetic acid / toluene / 15 h / Molecular sieve; Reflux
View Scheme
C10H18O3

C10H18O3

C19H27NO3

C19H27NO3

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / tetrahydrofuran; water / 12 h / 20 °C
2: acetic acid / toluene / 15 h / Molecular sieve; Reflux
View Scheme
6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
1745-07-9

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

2-acetyl-4-methylpentanal

2-acetyl-4-methylpentanal

C19H27NO3

C19H27NO3

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
With acetic acid In toluene for 15h; Molecular sieve; Reflux; Overall yield = 50 %; diastereoselective reaction;A n/a
B n/a
...Expand
6,7-dihydroxy-3,4-dihydroisoquinoline hydrochloride

6,7-dihydroxy-3,4-dihydroisoquinoline hydrochloride

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / methanol; water / 30 h / 65 - 70 °C / Large scale
2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 25 - 30 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / methanol; water
2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 25 - 30 °C / Large scale
View Scheme
2-acetyl-N,N,N,4-tetramethyl-1-pentanaminium iodide
1069-62-1

2-acetyl-N,N,N,4-tetramethyl-1-pentanaminium iodide

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / methanol; water / 30 h / 65 - 70 °C / Large scale
2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 25 - 30 °C / Large scale
View Scheme
3-methylene-5-methyl-2-hexanone
1187-87-7

3-methylene-5-methyl-2-hexanone

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / methanol; water
2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 25 - 30 °C / Large scale
View Scheme
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

2α-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine
3466-75-9, 7744-53-8, 7744-54-9, 85081-18-1, 113627-25-1

2α-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 1h; Inert atmosphere;80%
With sodium tetrahydroborate In ethanol at 20℃; for 12h; Inert atmosphere;51%
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

2β-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine
3466-75-9, 7744-53-8, 7744-54-9, 85081-18-1, 113627-25-1

2β-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran; ethanol at 0 - 20℃; for 0.5 - 6.5h; Product distribution / selectivity;67%
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

2α-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine
3466-75-9, 7744-53-8, 7744-54-9, 85081-18-1, 113627-25-1

2α-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

2β-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine
3466-75-9, 7744-53-8, 7744-54-9, 85081-18-1, 113627-25-1

2β-hydroxy-3-isobutyl-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

Conditions
ConditionsYield
Stage #1: (3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo<a>quinolizin-2-one</a> With sodium tetrahydroborate In ethanol at 0 - 3℃; for 3h; Inert atmosphere;
Stage #2: With water In dichloromethane		A n/a
B 8%
With sodium tetrahydroborate In ethanol at 0℃;
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

(+/-)-cyano-((2Ξ)-3t-isobutyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-yliden)-acetic acid ethyl ester
118660-30-3

(+/-)-cyano-((2Ξ)-3t-isobutyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-yliden)-acetic acid ethyl ester

Conditions
ConditionsYield
With ammonium acetate; acetic acid; toluene
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

malononitrile
109-77-3

malononitrile

(+/-)-(3t-isobutyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-ylidene)-malononitrile

(+/-)-(3t-isobutyl-9,10-dimethoxy-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-ylidene)-malononitrile

Conditions
ConditionsYield
With ammonium acetate; acetic acid; benzene
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

(+/-)-9,10-dihydroxy-3c-isobutyl-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one
89929-27-1

(+/-)-9,10-dihydroxy-3c-isobutyl-(11br)-1,3,4,6,7,11b-hexahydro-pyrido[2,1-a]isoquinolin-2-one

Conditions
ConditionsYield
With hydrogen bromide
isopropyllithium
1888-75-1

isopropyllithium

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

2α-isopropyl-2β-hydroxy-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

2α-isopropyl-2β-hydroxy-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

Conditions
ConditionsYield
With water 1.) THF, a) 0 deg C, 2.5 h, b) from 0 deg C to RT, 12 h; Yield given. Multistep reaction;
methyllithium
917-54-4

methyllithium

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

2α-hydroxy-2-methyl-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

2α-hydroxy-2-methyl-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

2β-hydroxy-2-methyl-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

2β-hydroxy-2-methyl-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

Conditions
ConditionsYield
With water 1.) THF, a) 0 deg C, 2.5 h, b) from 0 deg C to RT, 12 h; Yield given. Multistep reaction. Yields of byproduct given;
...Expand
ethyllithium
811-49-4

ethyllithium

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

2α-ethyl-2β-hydroxy-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

2α-ethyl-2β-hydroxy-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

Conditions
ConditionsYield
With water 1.) THF, a) 0 deg C, 2.5 h, b) from 0 deg C to RT, 12 h; Yield given. Multistep reaction;
propyllithium
2417-93-8

propyllithium

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

2α-n-propyl-2β-hydroxy-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

2α-n-propyl-2β-hydroxy-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

Conditions
ConditionsYield
With water 1.) THF, a) 0 deg C, 2.5 h, b) from 0 deg C to RT, 12 h; Yield given. Multistep reaction;
(2-methylpropyl)lithium
920-36-5, 90269-51-5

(2-methylpropyl)lithium

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

2α-isobutyl-2β-hydroxy-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

2α-isobutyl-2β-hydroxy-3-isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine

Conditions
ConditionsYield
With water 1.) THF, a) 0 deg C, 2.5 h, b) from 0 deg C to RT, 12 h; Yield given. Multistep reaction;
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

(3-isobutyl-9,10-dimethoxy-1,6,7,11b-tetrahydro-4H-pyrido[2,1-a]isoquinolin-2-yl)-acetic acid
115985-36-9

(3-isobutyl-9,10-dimethoxy-1,6,7,11b-tetrahydro-4H-pyrido[2,1-a]isoquinolin-2-yl)-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium acetate; acetic acid; benzene
2: aqueous HCl
View Scheme
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

A

(2R,3S,11bS)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol
924854-62-6

(2R,3S,11bS)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol

B

(+)-α-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol
924854-60-4

(+)-α-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran; ethanol at 0℃; for 1h; Product distribution / selectivity;
With L-Selectride In tetrahydrofuran at 0 - 20℃; for 6.5h; Product distribution / selectivity;
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

A

(3S,11bS)-tetrabenazine
1026016-84-1

(3S,11bS)-tetrabenazine

B

((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one)
1026016-83-0

((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one)

Conditions
ConditionsYield
Purification / work up; Resolution of racemate;
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

(3S,11bS)-tetrabenazine
1026016-84-1

(3S,11bS)-tetrabenazine

Conditions
ConditionsYield
Stage #1: (3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo<a>quinolizin-2-one</a> With (R)-10-camphorsulfonic acid In acetone Heating; Resolution of racemate;
Stage #2: With ammonium hydroxide In methanol
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one)
1026016-83-0

((3R,11bR)-3-isobutyl-9.10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one)

Conditions
ConditionsYield
Stage #1: (3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo<a>quinolizin-2-one</a> With (1S)-10-camphorsulfonic acid In acetone Heating; Resolution of racemate;
Stage #2: With ammonium hydroxide In methanol		3.4 g
Stage #1: (3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo<a>quinolizin-2-one</a> With (1S)-10-camphorsulfonic acid In acetone at 16 - 31℃; for 24h;
Stage #2: With sodium carbonate In diethyl ether; water pH=8;		83.12 g
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

RU 350
862377-27-3

RU 350

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: (1S)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: sodium tetrahydroborate
3.1: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
4.1: dimethylsulfide borane complex / tetrahydrofuran / 48 h / 0 - 15 °C
4.2: 1.5 h / pH 12 / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: (1S)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: ethanol; L-Selectride / tetrahydrofuran / 0.67 h / 0 °C
2.2: 20 °C
3.1: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
4.1: dimethylsulfide borane complex / tetrahydrofuran / 48 h / 0 - 15 °C
4.2: 1.5 h / pH 12 / Reflux
View Scheme
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

(2R,3R,11bS)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol
862377-29-5

(2R,3R,11bS)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: (R)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: ethanol; L-Selectride / tetrahydrofuran / 0.67 h / 0 °C
2.2: 20 °C
3.1: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
4.1: dimethylsulfide borane complex / tetrahydrofuran / 48 h / 0 - 15 °C
4.2: 1.5 h / pH 12 / Reflux
View Scheme
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

(11bR)-1,6,7,11b-tetrahydro-9,10-dimethoxy-3-(2-methylpropyl)-4H-benzo[a]quinolizine
920265-21-0

(11bR)-1,6,7,11b-tetrahydro-9,10-dimethoxy-3-(2-methylpropyl)-4H-benzo[a]quinolizine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (1S)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2: sodium tetrahydroborate
3: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1.1: (1S)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: ethanol; L-Selectride / tetrahydrofuran / 0.67 h / 0 °C
2.2: 20 °C
3.1: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
View Scheme
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

(11bS)-1,6,7,11b-tetrahydro-9,10-dimethoxy-3-(2-methylpropyl)-4H-benzo[a]quinolizine
1215167-80-8

(11bS)-1,6,7,11b-tetrahydro-9,10-dimethoxy-3-(2-methylpropyl)-4H-benzo[a]quinolizine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: (R)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: ethanol; L-Selectride / tetrahydrofuran / 0.67 h / 0 °C
2.2: 20 °C
3.1: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
View Scheme
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

(8aS,9aR,10aR)-5,8,8a,9a,10,10a-hexahydro-2,3-dimethoxy-8a-(2-methylpropyl)-6H-benz[a]oxireno[g]quinolizine
1300639-86-4

(8aS,9aR,10aR)-5,8,8a,9a,10,10a-hexahydro-2,3-dimethoxy-8a-(2-methylpropyl)-6H-benz[a]oxireno[g]quinolizine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: (1S)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: sodium tetrahydroborate
3.1: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
4.1: perchloric acid / methanol
4.2: 38 h / 20 °C / Darkness
View Scheme
Multi-step reaction with 4 steps
1.1: (1S)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: ethanol; L-Selectride / tetrahydrofuran / 0.67 h / 0 °C
2.2: 20 °C
3.1: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
4.1: perchloric acid / methanol
4.2: 38 h / 20 °C / Darkness
View Scheme
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

(8aR,9aS,10aS)-5,8,8a,9a,10,10a-hexahydro-2,3-dimethoxy-8a-(2-methylpropyl)-6H-benz[a]oxireno[g]quinolizine
1300639-88-6

(8aR,9aS,10aS)-5,8,8a,9a,10,10a-hexahydro-2,3-dimethoxy-8a-(2-methylpropyl)-6H-benz[a]oxireno[g]quinolizine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: (R)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: ethanol; L-Selectride / tetrahydrofuran / 0.67 h / 0 °C
2.2: 20 °C
3.1: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
4.1: perchloric acid / methanol
4.2: 38 h / 20 °C / Darkness
View Scheme
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

(2R,3S,11bS)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol
924854-62-6

(2R,3S,11bS)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: (R)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: ethanol; L-Selectride / tetrahydrofuran / 0.67 h / 0 °C
2.2: 20 °C
View Scheme
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

(2R,3S,11bR)-1,3,4,6,7,11b-hexahydro-9,10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol
862377-31-9

(2R,3S,11bR)-1,3,4,6,7,11b-hexahydro-9,10-methoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: (1S)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: sodium tetrahydroborate
3.1: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
4.1: perchloric acid / methanol
4.2: 38 h / 20 °C / Darkness
5.1: dimethylsulfide borane complex / tetrahydrofuran / 48 h / 0 - 15 °C
5.2: 0.5 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: (1S)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: ethanol; L-Selectride / tetrahydrofuran / 0.67 h / 0 °C
2.2: 20 °C
3.1: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
4.1: perchloric acid / methanol
4.2: 38 h / 20 °C / Darkness
5.1: dimethylsulfide borane complex / tetrahydrofuran / 48 h / 0 - 15 °C
5.2: 0.5 h / Reflux
View Scheme
(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one
58-46-8

(3R*,11bR*)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzoquinolizin-2-one

RU 346
862377-33-1

RU 346

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: (R)-10-camphorsulfonic acid / acetone / Heating; Resolution of racemate
2.1: ethanol; L-Selectride / tetrahydrofuran / 0.67 h / 0 °C
2.2: 20 °C
3.1: phosphorus pentachloride / dichloromethane / 0.5 h / 0 °C
4.1: perchloric acid / methanol
4.2: 38 h / 20 °C / Darkness
5.1: dimethylsulfide borane complex / tetrahydrofuran / 48 h / 0 - 15 °C
5.2: 0.5 h / Reflux
View Scheme

Tetrabenazine Specification

The Tetrabenazine, with the CAS registry number 58-46-8, is also known as 2H-Benzo[a]quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-, (3S,11bS)-. It belongs to the product categories of APIs; Serotonin Receptor; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 200-383-6. This chemical's molecular formula is C19H27NO3 and molecular weight is 317.42. What's more, both its IUPAC name and systematic name are the same which is called (3S,11bS)-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one. Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorder. When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and it is harmful if swallowed. 

Physical properties about Tetrabenazine are: (1)ACD/LogP: 3.476; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.48; (4)ACD/LogD (pH 7.4): 3.43; (5)ACD/BCF (pH 5.5): 25.96; (6)ACD/BCF (pH 7.4): 231.94; (7)ACD/KOC (pH 5.5): 186.36; (8)ACD/KOC (pH 7.4): 1665.24; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12) Polar Surface Area: 38.77 Å2; (13)Index of Refraction: 1.554; (14)Molar Refractivity: 90.255 cm3; (15)Molar Volume: 281.609 cm3; (16)Polarizability: 35.78×10-24cm3; (17)Surface Tension: 44.228 dyne/cm; (18)Density: 1.127 g/cm3; (19)Flash Point: 225.311 °C; (20)Enthalpy of Vaporization: 70.754 kJ/mol; (21)Boiling Point: 448.941 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C3[C@@H](CC(C)C)CN2[C@H](c1c(cc(OC)c(OC)c1)CC2)C3
(2) InChI: InChI=1S/C19H27NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16H,5-7,10-11H2,1-4H3/t14-,16-/m0/s1
(3) InChIKey: MKJIEFSOBYUXJB-HOCLYGCPSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 250mg/kg (250mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 intravenous 150mg/kg (150mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.
mouse LD50 oral 550mg/kg (550mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 308, 1972.
mouse LD50 subcutaneous 400mg/kg (400mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 308, 1972.

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