(R)-2-((R)-2-Acetoxy-2-phenyl-ethyl)-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (R)-2-((R)-2-Acetoxy-2-phenyl-ethyl)-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester
• CAS No.: 134040-18-9
• Molecular Formula: C₂₂H₂₉NO₆
• Molecular Weight: 403.475
• Mol file: 134040-18-9.mol

Synonyms:(R)-2-((R)-2-Acetoxy-2-phenyl-ethyl)-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester

Chemical Property of (R)-2-((R)-2-Acetoxy-2-phenyl-ethyl)-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((R)-2-Acetoxy-2-phenyl-ethyl)-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester

There total 17 articles about (R)-2-((R)-2-Acetoxy-2-phenyl-ethyl)-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-3,6-dihydro-2H-pyridine-1-carboxylic 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:

1-(carbomethoxy)-2-phenacylpiperidine (76469-99-3) → (R)-2-((R)-2-Acetoxy-2-phenyl-ethyl)-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester (134040-18-9)

Guidance literature:

Multi-step reaction with 8 steps

1: Li(tBuO)3AlH / tetrahydrofuran / 4 h / Heating

2: 100 percent / pyridine / 15 h / Ambient temperature

3: 343 mg / Et₄NOTs / 0.17 h / anodic methoxylation

4: 1) TiCl₄ / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, -78 deg C, 2h, then to r.t., 2h

5: 85 percent / Na, I₂ / 1 h

6: 43 percent / DBU / toluene / 4 h / 87 °C

7: 1) TiCl₄ / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, -78 deg C, 2h, to r.t. 2h

8: 64 mg / TsOH*H₂O / benzene / 16 h / Heating

With pyridine; iodine; sodium; titanium tetrachloride; tetraethylammonium tosylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; toluene; benzene;

DOI:10.1139/v91-034

Reference yield:

(R)-2-((R)-2-Hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid methyl ester (134040-02-1,134040-03-2) → (R)-2-((R)-2-Acetoxy-2-phenyl-ethyl)-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester (134040-18-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / pyridine / 15 h / Ambient temperature

2: 343 mg / Et₄NOTs / 0.17 h / anodic methoxylation

3: 1) TiCl₄ / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, -78 deg C, 2h, then to r.t., 2h

4: 85 percent / Na, I₂ / 1 h

5: 43 percent / DBU / toluene / 4 h / 87 °C

6: 1) TiCl₄ / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, -78 deg C, 2h, to r.t. 2h

7: 64 mg / TsOH*H₂O / benzene / 16 h / Heating

With pyridine; iodine; sodium; titanium tetrachloride; tetraethylammonium tosylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; benzene;

DOI:10.1139/v91-034

Reference yield:

(R)-2-((R)-2-Acetoxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid methyl ester (134040-04-3,134107-85-0) → (R)-2-((R)-2-Acetoxy-2-phenyl-ethyl)-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester (134040-18-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 343 mg / Et₄NOTs / 0.17 h / anodic methoxylation

2: 1) TiCl₄ / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, -78 deg C, 2h, then to r.t., 2h

3: 85 percent / Na, I₂ / 1 h

4: 43 percent / DBU / toluene / 4 h / 87 °C

5: 1) TiCl₄ / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, -78 deg C, 2h, to r.t. 2h

6: 64 mg / TsOH*H₂O / benzene / 16 h / Heating

With iodine; sodium; titanium tetrachloride; tetraethylammonium tosylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; benzene;

DOI:10.1139/v91-034

upstream raw materials:

(S)-2-((S)-2-Acetoxy-2-phenyl-ethyl)-6-(2-oxo-propyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester

ethylene glycol

(S)-2-((S)-2-Hydroxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid methyl ester

(S)-2-((S)-2-Acetoxy-2-phenyl-ethyl)-piperidine-1-carboxylic acid methyl ester

Downstream raw materials:

Episedacrine / Sedacrine

(R)-2-[(R)-1-Methyl-6-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-1-phenyl-ethanol

(-)-Sedacrine

6-Episedacrine