(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

Base Information

• Chemical Name: (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
• CAS No.: 276239-81-7
• Molecular Formula: C₁₉H₂₇NO₄
• Molecular Weight: 333.428
• Mol file: 276239-81-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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: 71.0%

(2S,2R,6S)-(+)-2-[2-(2-[1,3]-dioxolan-2-yl-ethyl)-6-methyl-3,6-dihydro-2H-pyridin-1-yl]-2-phenylethanol (276240-12-1) → (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)

Guidance literature:

With trifluoroacetic anhydride; In dichloromethane; water; trifluoroacetic acid; 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) → (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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; trifluoroacetic acid; 1: Grignard reaction / 2: Epoxidation;

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) → (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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; trifluoroacetic acid; 1: Grignard reaction / 2: Epoxidation;

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

upstream raw materials:

(2S,2R,6S)-(+)-2-[2-(2-[1,3]-dioxolan-2-yl-ethyl)-6-methyl-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

Downstream raw materials:

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