(1R,2S,3S,4R,6S)-(-)-6-[2-[1,3]-dioxolan-2-ylethyl]-1-(2-hydroxy-1-phenylethyl)-2,4-dimethylpiperidin-3-ol

Base Information

• Chemical Name: (1R,2S,3S,4R,6S)-(-)-6-[2-[1,3]-dioxolan-2-ylethyl]-1-(2-hydroxy-1-phenylethyl)-2,4-dimethylpiperidin-3-ol
• CAS No.: 276239-82-8
• Molecular Formula: C₂₀H₃₁NO₄
• Molecular Weight: 349.47
• Mol file: 276239-82-8.mol

Synonyms:(1R,2S,3S,4R,6S)-(-)-6-[2-[1,3]-dioxolan-2-ylethyl]-1-(2-hydroxy-1-phenylethyl)-2,4-dimethylpiperidin-3-ol

Chemical Property of (1R,2S,3S,4R,6S)-(-)-6-[2-[1,3]-dioxolan-2-ylethyl]-1-(2-hydroxy-1-phenylethyl)-2,4-dimethylpiperidin-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3S,4R,6S)-(-)-6-[2-[1,3]-dioxolan-2-ylethyl]-1-(2-hydroxy-1-phenylethyl)-2,4-dimethylpiperidin-3-ol

There total 5 articles about (1R,2S,3S,4R,6S)-(-)-6-[2-[1,3]-dioxolan-2-ylethyl]-1-(2-hydroxy-1-phenylethyl)-2,4-dimethylpiperidin-3-ol 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: 57.0%

methyllithium (917-54-4) + (2S,2R,4S,5R,6S)-(+)-2-{2-[2-[1,3]-dioxolan-2-yl-ethyl]-6-methyl-4,5-epoxy-3,6-dihydro-2H-pyridin-1-yl}-2-phenylethanol (276239-81-7) → (1R,2S,3S,4R,6S)-(-)-6-[2-[1,3]-dioxolan-2-ylethyl]-1-(2-hydroxy-1-phenylethyl)-2,4-dimethylpiperidin-3-ol (276239-82-8)

Guidance literature:

With copper(l) iodide; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1391::AID-EJOC1391>3.0.CO;2-D

Reference yield:

1,3-dioxolan-2-ylethylmagnesium bromide (37610-80-3) → (1R,2S,3S,4R,6S)-(-)-6-[2-[1,3]-dioxolan-2-ylethyl]-1-(2-hydroxy-1-phenylethyl)-2,4-dimethylpiperidin-3-ol (276239-82-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 47 percent / tetrahydrofuran / 7 h / 0 - 20 °C

2: 71 percent / 50percent H₂O₂; (CF₃CO)2O / trifluoroacetic acid; CH₂Cl₂; H₂O / 0 - 20 °C

3: 57 percent / CuI / diethyl ether; tetrahydrofuran / 0 - 20 °C

With copper(l) iodide; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; dichloromethane; water; trifluoroacetic acid; 1: Grignard reaction / 2: Epoxidation / 3: Methylation;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1391::AID-EJOC1391>3.0.CO;2-D

Reference yield:

(3R,5S,8aR)-5-methyl-3-phenyl-2,3,8,8a-tetrahydro-2H-oxazolo[3,2-a]pyridine (276239-73-7) → (1R,2S,3S,4R,6S)-(-)-6-[2-[1,3]-dioxolan-2-ylethyl]-1-(2-hydroxy-1-phenylethyl)-2,4-dimethylpiperidin-3-ol (276239-82-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 47 percent / tetrahydrofuran / 7 h / 0 - 20 °C

2: 71 percent / 50percent H₂O₂; (CF₃CO)2O / trifluoroacetic acid; CH₂Cl₂; H₂O / 0 - 20 °C

3: 57 percent / CuI / diethyl ether; tetrahydrofuran / 0 - 20 °C

With copper(l) iodide; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; dichloromethane; water; trifluoroacetic acid; 1: Grignard reaction / 2: Epoxidation / 3: Methylation;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1391::AID-EJOC1391>3.0.CO;2-D

upstream raw materials:

methyllithium

(2S,2R,4S,5R,6S)-(+)-2-{2-[2-[1,3]-dioxolan-2-yl-ethyl]-6-methyl-4,5-epoxy-3,6-dihydro-2H-pyridin-1-yl}-2-phenylethanol

1,3-dioxolan-2-ylethylmagnesium bromide

(3R,5S,8aR)-5-methyl-3-phenyl-2,3,8,8a-tetrahydro-2H-oxazolo[3,2-a]pyridine