1-(1,3-Benzodioxol-5-ylmethyl)-6,7-dimethoxy-4-[(2S)-1-methylpyrrolidin-2-yl]isoquinoline

Base Information

• Chemical Name: 1-(1,3-Benzodioxol-5-ylmethyl)-6,7-dimethoxy-4-[(2S)-1-methylpyrrolidin-2-yl]isoquinoline
• CAS No.: 53912-94-0
• Molecular Formula: C24H26N2O4
• Molecular Weight: 406.4742
• Mol file: 53912-94-0.mol

Synonyms:

Chemical Property of 1-(1,3-Benzodioxol-5-ylmethyl)-6,7-dimethoxy-4-[(2S)-1-methylpyrrolidin-2-yl]isoquinoline

Chemical Property:

• Vapor Pressure: 2.99E-12mmHg at 25°C
• Melting Point: 107-110°C
• Boiling Point: 552.5°Cat760mmHg
• Flash Point: 287.9°C
• PSA: 53.05000
• Density: 1.232g/cm³
• LogP: 4.27610

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: This newly discovered alkaloid has been isolated from Papaver macrostomum. It crystallizes as colourless rods from C6H6 and is laevorotatory with a specific rotation of [α]25D - 51 ° ± 3° (c 0.892, CHCI3). It gives a complex ultraviolet spectrum in EtOH with absorption maxima at 241,288,317 and 332 nm with shoulders at 246, 276 and 292 nm. In the presence of dilute acid, these absorption maxima appear at 259, 290 and 319 nm with a shoulder at 333 nm. Macrostomine is found in the non-quaternary fraction of the alkaloidal extract. It gives a negative Cotton effect which leads to the assumption that the configuration is S. The alkaloid forms a crystalline methiodide with m.p. 220-230°C as slender needles when crystallized from EtOH. The structure given has been determined from chemical and spectroscopic data.

Technology Process of 1-(1,3-Benzodioxol-5-ylmethyl)-6,7-dimethoxy-4-[(2S)-1-methylpyrrolidin-2-yl]isoquinoline

There total 18 articles about 1-(1,3-Benzodioxol-5-ylmethyl)-6,7-dimethoxy-4-[(2S)-1-methylpyrrolidin-2-yl]isoquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

(S)-1-chloro-6,7-dimethoxy-4-(1-methylpyrrolidin-2-yl)isoquinoline (1252608-25-5) + (benzo[d][1,3]dioxol-5-ylmethyl)magnesium chloride → Macrostomin (53912-94-0)

Guidance literature:

With bis(acetylacetonate)nickel(II); In tetrahydrofuran; at 20 ℃; for 96h; Inert atmosphere;

DOI:10.1021/ol101887b

Reference yield:

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) → Macrostomin (53912-94-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / 16 h / 150 °C

2: 93 percent / Hg(ClO₄)2 trihydrate / methanol; diethyl ether / 1 h / Ambient temperature

3: POCl₃ / acetonitrile / 4 h / Heating

4: 10percent Pd/C / 1,2,3,4-tetrahydro-naphthalene / 3 h / 190 - 200 °C

5: Et₃N / benzene / 1) 0 deg C, 30 min, 2) reflux, 3 h

6: 2) 2N HCl / 1) CH₂Cl₂, a) 0 deg C, 1h, b) r.t., 3 h, 2) 2 h, r.t.

7: H₂O / 2 h / Heating

8: 92 percent / Raney-Ni, NH₃ / ethanol / 5 h / 40 - 45 °C

9: 1) NaBH₄/N-benzoyloxycarbonyl-L-proline / 1) CHCl₂, a) 0 deg C, 2 h, b) r.t., 60 h, 2a) 0 deg C, 15 min, 2b) r.t., 15 min, 2c) 70 deg C, 40 min

10: LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 15 min, 2) r.t., 15 min, 3) reflux, 40 min

With hydrogenchloride; sodium tetrahydroborate; palladium on activated charcoal; lithium aluminium tetrahydride; mercury(II) perchlorate; N-benzoyloxycarbonyl-L-proline; ammonia; nickel; triethylamine; trichlorophosphate; In tetrahydrofuran; methanol; tetralin; diethyl ether; ethanol; water; acetonitrile; benzene;

DOI:10.1002/ardp.19913240504

Reference yield:

α-(3,4-dimethoxyphenyl)-α-(2-methyl-1,3-dithiolan-2-yl)acetonitrile (134993-16-1) → Macrostomin (53912-94-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 97 percent / B₂H₆-tetrahydrofuran complex / tetrahydrofuran / 0.75 h / Heating

2: 93 percent / 16 h / 150 °C

3: 93 percent / Hg(ClO₄)2 trihydrate / methanol; diethyl ether / 1 h / Ambient temperature

4: POCl₃ / acetonitrile / 4 h / Heating

5: 10percent Pd/C / 1,2,3,4-tetrahydro-naphthalene / 3 h / 190 - 200 °C

6: Et₃N / benzene / 1) 0 deg C, 30 min, 2) reflux, 3 h

7: 2) 2N HCl / 1) CH₂Cl₂, a) 0 deg C, 1h, b) r.t., 3 h, 2) 2 h, r.t.

8: H₂O / 2 h / Heating

9: 92 percent / Raney-Ni, NH₃ / ethanol / 5 h / 40 - 45 °C

10: 1) NaBH₄/N-benzoyloxycarbonyl-L-proline / 1) CHCl₂, a) 0 deg C, 2 h, b) r.t., 60 h, 2a) 0 deg C, 15 min, 2b) r.t., 15 min, 2c) 70 deg C, 40 min

11: LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 15 min, 2) r.t., 15 min, 3) reflux, 40 min

With hydrogenchloride; sodium tetrahydroborate; palladium on activated charcoal; lithium aluminium tetrahydride; mercury(II) perchlorate; B₂H₆-THF; N-benzoyloxycarbonyl-L-proline; ammonia; nickel; triethylamine; trichlorophosphate; In tetrahydrofuran; methanol; tetralin; diethyl ether; ethanol; water; acetonitrile; benzene;

DOI:10.1002/ardp.19913240504

upstream raw materials:

N-formylnormacrostomine

macrostomine N-oxide

benzo[1,3]dioxol-5-yl-acetic acid methyl ester

α-(3,4-dimethoxyphenyl)-α-(2-methyl-1,3-dithiolan-2-yl)acetonitrile

Refernces

• 1、 Enamorado, Monica F.,Ondachi, Pauline W.,Comins, Daniel L.. "A five-step synthesis of (S)-macrostomine from (S)-nicotine". supporting information; experimental part. p. 4513 - 4515. Retrieved 2010/12/25.