[(2R,6R)-6-((1R,2S)-1,2-Bis-methoxymethoxy-heptyl)-1-(3-{(toluene-4-sulfonyl)-[4-(2,2,2-trifluoro-acetylamino)-butyl]-amino}-propyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-acetic acid methyl ester

Base Information

• Chemical Name: [(2R,6R)-6-((1R,2S)-1,2-Bis-methoxymethoxy-heptyl)-1-(3-{(toluene-4-sulfonyl)-[4-(2,2,2-trifluoro-acetylamino)-butyl]-amino}-propyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-acetic acid methyl ester
• CAS No.: 91377-26-3
• Molecular Formula: C₃₅H₅₆F₃N₃O₉S
• Molecular Weight: 751.906

Synonyms:

Chemical Property of [(2R,6R)-6-((1R,2S)-1,2-Bis-methoxymethoxy-heptyl)-1-(3-{(toluene-4-sulfonyl)-[4-(2,2,2-trifluoro-acetylamino)-butyl]-amino}-propyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,6R)-6-((1R,2S)-1,2-Bis-methoxymethoxy-heptyl)-1-(3-{(toluene-4-sulfonyl)-[4-(2,2,2-trifluoro-acetylamino)-butyl]-amino}-propyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-acetic acid methyl ester

There total 14 articles about [(2R,6R)-6-((1R,2S)-1,2-Bis-methoxymethoxy-heptyl)-1-(3-{(toluene-4-sulfonyl)-[4-(2,2,2-trifluoro-acetylamino)-butyl]-amino}-propyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-acetic acid methyl ester 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:

N-(toluene-4-sulfonyl)-β-alanyl chloride (61341-03-5) → [(2R,6R)-6-((1R,2S)-1,2-Bis-methoxymethoxy-heptyl)-1-(3-{(toluene-4-sulfonyl)-[4-(2,2,2-trifluoro-acetylamino)-butyl]-amino}-propyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-acetic acid methyl ester (91377-26-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / K₂CO₃ / benzene; toluene; H₂O / 0 - 10 °C

2: 85 percent / LiAlH₄ / tetrahydrofuran / Heating

3: 96 percent / K₂CO₃ / dimethylformamide / Ambient temperature

4: 80percent aq. NH₂NH₂ / ethanol / Ambient temperature

5: 70 percent / Et₃N / CH₂Cl₂ / -78 °C

With lithium aluminium tetrahydride; potassium carbonate; hydrazine hydrate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(01)80076-9

Reference yield:

(2R,6S)-6-((1S,2R)-1,2-Bis-methoxymethoxy-heptyl)-2-(2,2-diethoxy-ethyl)-1,2,3,6-tetrahydro-pyridine → [(2R,6R)-6-((1R,2S)-1,2-Bis-methoxymethoxy-heptyl)-1-(3-{(toluene-4-sulfonyl)-[4-(2,2,2-trifluoro-acetylamino)-butyl]-amino}-propyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-acetic acid methyl ester (91377-26-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / K₂CO₃ / benzene; toluene; H₂O / 0 - 10 °C

2: 85 percent / LiAlH₄ / tetrahydrofuran / Heating

3: 96 percent / K₂CO₃ / dimethylformamide / Ambient temperature

4: 80percent aq. NH₂NH₂ / ethanol / Ambient temperature

5: 70 percent / Et₃N / CH₂Cl₂ / -78 °C

With lithium aluminium tetrahydride; potassium carbonate; hydrazine hydrate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(01)80076-9

Reference yield:

(2R,3R,6S)-2-((1R,2S)-1,2-Bis-methoxymethoxy-heptyl)-6-(2,2-diethoxy-ethyl)-3-hydroxy-piperidine-1-carboxylic acid benzyl ester → [(2R,6R)-6-((1R,2S)-1,2-Bis-methoxymethoxy-heptyl)-1-(3-{(toluene-4-sulfonyl)-[4-(2,2,2-trifluoro-acetylamino)-butyl]-amino}-propyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-acetic acid methyl ester (91377-26-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / pyridine / Ambient temperature

2: 81 percent / 1,8-diazabicyclo>5.4.0>undec-7-ene / toluene / 20 h / 110 - 115 °C

3: Na / liquid ammonia; tetrahydrofuran / -70 - -60 °C

4: 87 percent / K₂CO₃ / benzene; toluene; H₂O / 0 - 10 °C

5: 85 percent / LiAlH₄ / tetrahydrofuran / Heating

6: 96 percent / K₂CO₃ / dimethylformamide / Ambient temperature

7: 80percent aq. NH₂NH₂ / ethanol / Ambient temperature

8: 70 percent / Et₃N / CH₂Cl₂ / -78 °C

With lithium aluminium tetrahydride; sodium; potassium carbonate; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; pyridine; ethanol; dichloromethane; ammonia; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(01)80076-9

upstream raw materials:

diazomethane

N-{4-[{3-[(2S,6R)-6-((1R,2S)-1,2-Bis-methoxymethoxy-heptyl)-2-(2,2-diethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide

N-(toluene-4-sulfonyl)-β-alanyl chloride

(2S,6R)-6-((1R,2S)-1,2-Bis-methoxymethoxy-heptyl)-2-(2,2-diethoxy-ethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

Downstream raw materials:

(4R,15aR)-4-((1R,2S)-1,2-Dihydroxy-heptyl)-8-(toluene-4-sulfonyl)-1,4,6,7,8,9,10,11,12,13,15,15a-dodecahydro-5H-4a,8,13-triaza-benzocyclotridecen-14-one

(+/-)-cannabisativine

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