Product Name

  • Name

    Mesembrine

  • EINECS
  • CAS No. 468-53-1
  • Article Data26
  • CAS DataBase
  • Density 1.133 g/cm3
  • Solubility
  • Melting Point
  • Formula C17H23NO3
  • Boiling Point 419.2 °C at 760 mmHg
  • Molecular Weight 289.375
  • Flash Point 207.3 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 468-53-1 (Mesembrine)
  • Hazard Symbols
  • Synonyms 3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-6H-indol-6-one;(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one;
  • PSA 38.77000
  • LogP 2.33660

Synthetic route

t-butyl 2-((S)-1-(3,4-dimethoxyphenyl)-4-oxocyclohex-2-enyl)ethylmethylcarbamate

t-butyl 2-((S)-1-(3,4-dimethoxyphenyl)-4-oxocyclohex-2-enyl)ethylmethylcarbamate

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 1.33333h;81%
(R)-3a-(3,4-dimethoxyphenyl)-1-methyl-1,2,3,3a,4,5-hexahydro-6H-indol-6-one

(R)-3a-(3,4-dimethoxyphenyl)-1-methyl-1,2,3,3a,4,5-hexahydro-6H-indol-6-one

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With ammonium hydroxide; lithium In tetrahydrofuran; tert-butyl alcohol for 0.5h; Birch Reduction; Inert atmosphere;77%
With ammonia; lithium In tetrahydrofuran; tert-butyl alcohol at -78℃; for 0.75h;77%
(3aR,8bS)-3a-(3,4-dimethoxyphenyl)-1,6-dimethyl-1,2,3,3a,4,5,6,8b-octahydro-8H-isoxazolo[3,4-g]indol-8-one
911847-34-2

(3aR,8bS)-3a-(3,4-dimethoxyphenyl)-1,6-dimethyl-1,2,3,3a,4,5,6,8b-octahydro-8H-isoxazolo[3,4-g]indol-8-one

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With hexacarbonyl molybdenum In water; acetonitrile for 12h; Heating;75%
(3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol
1427472-33-0

(3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With dipyridinium dichromate In dichloromethane at 20℃; for 2h; Inert atmosphere;48%
(R)-2-(3,4-Dimethoxy-phenyl)-2-(2-methylamino-ethyl)-5-oxo-hexanal
99548-21-7

(R)-2-(3,4-Dimethoxy-phenyl)-2-(2-methylamino-ethyl)-5-oxo-hexanal

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With sodium hydroxide Ambient temperature;
C19H27NO4

C19H27NO4

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With acid Yield given;
[(S)-1-(3,4-Dimethoxy-phenyl)-3-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-4-oxo-cyclohex-2-enyl]-acetaldehyde
911847-30-8

[(S)-1-(3,4-Dimethoxy-phenyl)-3-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-4-oxo-cyclohex-2-enyl]-acetaldehyde

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / 1,2-dichloro-ethane / 0.08 h / 20 °C
2: 190 mg / NaBH3CN / 1,2-dichloro-ethane / 6 h / 20 °C
3: 60 percent / ethanol / 6 h / Heating
4: 75 percent / Mo(CO)6 / acetonitrile; H2O / 12 h / Heating
View Scheme
(S)-4-(3,4-Dimethoxy-phenyl)-2-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-4-{2-[(E)-methylimino]-ethyl}-cyclohex-2-enone

(S)-4-(3,4-Dimethoxy-phenyl)-2-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-4-{2-[(E)-methylimino]-ethyl}-cyclohex-2-enone

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 190 mg / NaBH3CN / 1,2-dichloro-ethane / 6 h / 20 °C
2: 60 percent / ethanol / 6 h / Heating
3: 75 percent / Mo(CO)6 / acetonitrile; H2O / 12 h / Heating
View Scheme
((R)-1-allyl-5-(3,4-dimethoxyphenyl)-2-methoxycyclohexa-2,5-dienyl)((S)-2-(methoxymethyl)pyrrolidin-1-yl)methanone
911847-24-0

((R)-1-allyl-5-(3,4-dimethoxyphenyl)-2-methoxycyclohexa-2,5-dienyl)((S)-2-(methoxymethyl)pyrrolidin-1-yl)methanone

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 95 percent / HCl / methanol / 15 h / 20 °C
2.1: 80 percent / 1,2-dichloro-benzene / 10 h / Heating
3.1: O3; Sudan III / methanol / 0.03 h / -78 °C
3.2: dimethyl sulfide / methanol / 7 h / 20 °C
4.1: triethylamine / 1,2-dichloro-ethane / 0.08 h / 20 °C
5.1: 190 mg / NaBH3CN / 1,2-dichloro-ethane / 6 h / 20 °C
6.1: 60 percent / ethanol / 6 h / Heating
7.1: 75 percent / Mo(CO)6 / acetonitrile; H2O / 12 h / Heating
View Scheme
(S)-4-allyl-4-(3,4-dimethoxyphenyl)-2-((S)-2-(methoxymethyl)pyrrolidin-1-carbonyl)cyclohex-2-en-1-one
911847-28-4

(S)-4-allyl-4-(3,4-dimethoxyphenyl)-2-((S)-2-(methoxymethyl)pyrrolidin-1-carbonyl)cyclohex-2-en-1-one

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: O3; Sudan III / methanol / 0.03 h / -78 °C
1.2: dimethyl sulfide / methanol / 7 h / 20 °C
2.1: triethylamine / 1,2-dichloro-ethane / 0.08 h / 20 °C
3.1: 190 mg / NaBH3CN / 1,2-dichloro-ethane / 6 h / 20 °C
4.1: 60 percent / ethanol / 6 h / Heating
5.1: 75 percent / Mo(CO)6 / acetonitrile; H2O / 12 h / Heating
View Scheme
(R)-2-allyl-4-(3,4-dimethoxyphenyl)-2-((S)-2-(methoxymethyl)pyrrolidin-1-carbonyl)cyclohex-3-en-1-one
911847-26-2

(R)-2-allyl-4-(3,4-dimethoxyphenyl)-2-((S)-2-(methoxymethyl)pyrrolidin-1-carbonyl)cyclohex-3-en-1-one

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 80 percent / 1,2-dichloro-benzene / 10 h / Heating
2.1: O3; Sudan III / methanol / 0.03 h / -78 °C
2.2: dimethyl sulfide / methanol / 7 h / 20 °C
3.1: triethylamine / 1,2-dichloro-ethane / 0.08 h / 20 °C
4.1: 190 mg / NaBH3CN / 1,2-dichloro-ethane / 6 h / 20 °C
5.1: 60 percent / ethanol / 6 h / Heating
6.1: 75 percent / Mo(CO)6 / acetonitrile; H2O / 12 h / Heating
View Scheme
(3aR,7aR)-3a-(3,4-dimethoxyphenyl)-7-((S)-2-(methoxymethyl)pyrrolidin-1-carbonyl)-1-methylhexahydro-1H-indol-6(2H)-one
911847-32-0

(3aR,7aR)-3a-(3,4-dimethoxyphenyl)-7-((S)-2-(methoxymethyl)pyrrolidin-1-carbonyl)-1-methylhexahydro-1H-indol-6(2H)-one

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / ethanol / 6 h / Heating
2: 75 percent / Mo(CO)6 / acetonitrile; H2O / 12 h / Heating
View Scheme
2-(but-3'-ynyl)-2-methyl-1,3-dioxolane
42541-87-7

2-(but-3'-ynyl)-2-methyl-1,3-dioxolane

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: EtMgBr / diethyl ether; toluene
2: 1.) n-BuLi, 2.) CuBr
3: 1.) Zn-Cu, 2.) Zn, AcOH / 1.) THF, 0 deg C, 2.) RT, 1 h
4: aq. AcOH / 2 h / 60 °C
5: K2CO3 / methanol
6: methanol
7: 83 percent / tetrahydrofuran / Heating
8: PTS
9: LiAlH4 / tetrahydrofuran
10: acid
View Scheme
(3aR,7aR)-3a-(3,4-Dimethoxy-phenyl)-1-methyl-hexahydro-indole-2,6-dione
151764-32-8

(3aR,7aR)-3a-(3,4-Dimethoxy-phenyl)-1-methyl-hexahydro-indole-2,6-dione

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: PTS
2: LiAlH4 / tetrahydrofuran
3: acid
View Scheme
3'a-(3,4-dimethoxy-phenyl)-1'-methyl-hexahydro-spiro[[1,3]dioxolane-2,6'-indol]-2'-one
21104-36-9, 80515-96-4

3'a-(3,4-dimethoxy-phenyl)-1'-methyl-hexahydro-spiro[[1,3]dioxolane-2,6'-indol]-2'-one

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4 / tetrahydrofuran
2: acid
View Scheme
2-Methyl-2-[4-((S)-toluene-4-sulfinyl)-but-3-ynyl]-[1,3]dioxolane
151670-66-5

2-Methyl-2-[4-((S)-toluene-4-sulfinyl)-but-3-ynyl]-[1,3]dioxolane

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 1.) n-BuLi, 2.) CuBr
2: 1.) Zn-Cu, 2.) Zn, AcOH / 1.) THF, 0 deg C, 2.) RT, 1 h
3: aq. AcOH / 2 h / 60 °C
4: K2CO3 / methanol
5: methanol
6: 83 percent / tetrahydrofuran / Heating
7: PTS
8: LiAlH4 / tetrahydrofuran
9: acid
View Scheme
[(S)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-acetic acid

[(S)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-acetic acid

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: methanol
2: 83 percent / tetrahydrofuran / Heating
3: PTS
4: LiAlH4 / tetrahydrofuran
5: acid
View Scheme
[(S)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-acetic acid methyl ester
151764-31-7

[(S)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-acetic acid methyl ester

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 83 percent / tetrahydrofuran / Heating
2: PTS
3: LiAlH4 / tetrahydrofuran
4: acid
View Scheme
2-[(E)-3-(3,4-Dimethoxy-phenyl)-4-((R)-toluene-4-sulfinyl)-but-3-enyl]-2-methyl-[1,3]dioxolane
151670-58-5

2-[(E)-3-(3,4-Dimethoxy-phenyl)-4-((R)-toluene-4-sulfinyl)-but-3-enyl]-2-methyl-[1,3]dioxolane

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1.) Zn-Cu, 2.) Zn, AcOH / 1.) THF, 0 deg C, 2.) RT, 1 h
2: aq. AcOH / 2 h / 60 °C
3: K2CO3 / methanol
4: methanol
5: 83 percent / tetrahydrofuran / Heating
6: PTS
7: LiAlH4 / tetrahydrofuran
8: acid
View Scheme
(4R,5R)-4-(3,4-Dimethoxy-phenyl)-4-(3-oxo-butyl)-5-p-tolylsulfanyl-dihydro-furan-2-one

(4R,5R)-4-(3,4-Dimethoxy-phenyl)-4-(3-oxo-butyl)-5-p-tolylsulfanyl-dihydro-furan-2-one

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: K2CO3 / methanol
2: methanol
3: 83 percent / tetrahydrofuran / Heating
4: PTS
5: LiAlH4 / tetrahydrofuran
6: acid
View Scheme
(4R,5R)-4-(3,4-Dimethoxy-phenyl)-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one

(4R,5R)-4-(3,4-Dimethoxy-phenyl)-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-5-p-tolylsulfanyl-dihydro-furan-2-one

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: aq. AcOH / 2 h / 60 °C
2: K2CO3 / methanol
3: methanol
4: 83 percent / tetrahydrofuran / Heating
5: PTS
6: LiAlH4 / tetrahydrofuran
7: acid
View Scheme
(3aR,5aR,8S,9aR)-3a-(3,4-Dimethoxy-phenyl)-8-isopropyl-1,5a-dimethyl-decahydro-oxazolo[3,2-a]pyrrolo[3,2-e]pyridine
99548-20-6

(3aR,5aR,8S,9aR)-3a-(3,4-Dimethoxy-phenyl)-8-isopropyl-1,5a-dimethyl-decahydro-oxazolo[3,2-a]pyrrolo[3,2-e]pyridine

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Bu4NH2PO4 / ethanol
2: 4N NaOH / Ambient temperature
View Scheme
[(3S,6R,8aR)-6-(3,4-Dimethoxy-phenyl)-3-isopropyl-8a-methyl-5-oxo-hexahydro-oxazolo[3,2-a]pyridin-6-yl]-acetaldehyde

[(3S,6R,8aR)-6-(3,4-Dimethoxy-phenyl)-3-isopropyl-8a-methyl-5-oxo-hexahydro-oxazolo[3,2-a]pyridin-6-yl]-acetaldehyde

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: CNBH3(-)
2: LiAl(OEt)H3 / 1,2-dimethoxy-ethane; toluene / -20 °C
3: Bu4NH2PO4 / ethanol
4: 4N NaOH / Ambient temperature
View Scheme
(3S,6R,8aR)-6-(3,4-Dimethoxy-phenyl)-3-isopropyl-8a-methyl-6-(2-methylamino-ethyl)-hexahydro-oxazolo[3,2-a]pyridin-5-one
99548-18-2

(3S,6R,8aR)-6-(3,4-Dimethoxy-phenyl)-3-isopropyl-8a-methyl-6-(2-methylamino-ethyl)-hexahydro-oxazolo[3,2-a]pyridin-5-one

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: LiAl(OEt)H3 / 1,2-dimethoxy-ethane; toluene / -20 °C
2: Bu4NH2PO4 / ethanol
3: 4N NaOH / Ambient temperature
View Scheme
(S)-6-(3,4-Dimethoxy-phenyl)-3-isopropyl-8a-methyl-hexahydro-oxazolo[3,2-a]pyridin-5-one
99548-16-0, 99603-20-0, 99603-21-1, 99603-22-2

(S)-6-(3,4-Dimethoxy-phenyl)-3-isopropyl-8a-methyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / s-BuLi / tetrahydrofuran / -20 °C
2: OsO4, NaIO4 / diethyl ether; H2O / 8 h / 25 °C
3: CNBH3(-)
4: LiAl(OEt)H3 / 1,2-dimethoxy-ethane; toluene / -20 °C
5: Bu4NH2PO4 / ethanol
6: 4N NaOH / Ambient temperature
View Scheme
(3S,6R,8aR)-6-Allyl-6-(3,4-dimethoxy-phenyl)-3-isopropyl-8a-methyl-hexahydro-oxazolo[3,2-a]pyridin-5-one
99548-17-1

(3S,6R,8aR)-6-Allyl-6-(3,4-dimethoxy-phenyl)-3-isopropyl-8a-methyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: OsO4, NaIO4 / diethyl ether; H2O / 8 h / 25 °C
2: CNBH3(-)
3: LiAl(OEt)H3 / 1,2-dimethoxy-ethane; toluene / -20 °C
4: Bu4NH2PO4 / ethanol
5: 4N NaOH / Ambient temperature
View Scheme
(3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-amine
853761-21-4

(3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-amine

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Stage #1: (3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-amine With 3,5-di-tert-butyl-o-benzoquinone In tetrahydrofuran; methanol for 1h;
Stage #2: With oxalic acid In tetrahydrofuran; methanol; water
Stage #3: With potassium hydroxide In tetrahydrofuran; methanol; water
1-(3,4-Dimethoxy-phenyl)-1-methyl-iminomethyl-cyclopropan
20802-17-9

1-(3,4-Dimethoxy-phenyl)-1-methyl-iminomethyl-cyclopropan

methyl vinyl ketone
78-94-4

methyl vinyl ketone

A

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

B

(-)-mesembrine
468-53-1, 6023-73-0, 21104-37-0, 24880-43-1, 28639-24-9, 35056-46-3, 35056-47-4

(-)-mesembrine

Conditions
ConditionsYield
Stage #1: 1-(3,4-Dimethoxy-phenyl)-1-methyl-iminomethyl-cyclopropan With chloro-trimethyl-silane; sodium iodide In DMF (N,N-dimethyl-formamide) at 90℃; for 3h;
Stage #2: With hydrogenchloride In diethyl ether; dichloromethane
Stage #3: methyl vinyl ketone With sodium hydroxide more than 3 stages;
...Expand
2-bromo-4,5-dimethoxy-N-((1R,5S)-2-methylene-5-(prop-1-en-2-yl)cyclohexyl)benzene sulfonamide
1427435-77-5

2-bromo-4,5-dimethoxy-N-((1R,5S)-2-methylene-5-(prop-1-en-2-yl)cyclohexyl)benzene sulfonamide

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one
468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C
1.2: 15 h / 0 - 20 °C
2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 15 h / 40 °C
3.1: palladium diacetate; triphenylphosphine; potassium carbonate / N,N-dimethyl-formamide / 15 h / 110 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 15 h / 20 °C
4.2: 15 h / 0 - 20 °C
5.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 19 h / 20 °C / 760.05 Torr
6.1: 3-chloro-benzenecarboperoxoic acid / chloroform-d1; water-d2 / 48 h / 20 °C
7.1: lithium; ammonia / tetrahydrofuran / -78 - 20 °C / Inert atmosphere
7.2: 4 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Inert atmosphere; Reflux
9.1: dipyridinium dichromate / dichloromethane / 2 h / 20 °C / Inert atmosphere
View Scheme

Mesembrine Specification

The Mesembrine, with the CAS registry number 468-53-1, is also known as 3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-6H-indol-6-one. The molecular formula of this chemical is C17H23NO3 and molecular weight is 289.3694. What's more, its IUPAC name is (3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one. In addition, it should be stored in condition of cold and dry. It has been shown to act as a serotonin reuptake inhibitor, and more recently, has also been found to behave as a weak inhibitor of the enzyme phosphodiesterase 4 (PDE4).

Physical properties about Mesembrine are: (1)ACD/LogP: 1.952; (2)ACD/LogD (pH 5.5): -0.93; (3)ACD/LogD (pH 7.4): 0.56; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 11.21; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.548; (11)Molar Refractivity: 81.053 cm3; (12)Molar Volume: 255.188 cm3; (13)Polarizability: 32.132 10-24cm3; (14)Surface Tension: 41.6389999389648 dyne/cm; (15)Density: 1.134 g/cm3; (16)Flash Point: 207.329 °C; (17)Enthalpy of Vaporization: 67.287 kJ/mol; (18)Boiling Point: 419.206 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1) SMILES: O=C3CC[C@@]2(c1ccc(OC)c(OC)c1)[C@H](N(CC2)C)C3
(2) InChI: InChI=1/C17H23NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-5,10,16H,6-9,11H2,1-3H3/t16-,17-/m1/s1
(3) InChIKey: DAHIQPJTGIHDGO-IAGOWNOFBH

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