8a(R)-methyl (8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ylidene)acetate

Base Information

• Chemical Name: 8a(R)-methyl (8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ylidene)acetate
• CAS No.: 163813-49-8
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.359
• Mol file: 163813-49-8.mol

Synonyms:8a(R)-methyl (8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ylidene)acetate

Chemical Property of 8a(R)-methyl (8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ylidene)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8a(R)-methyl (8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ylidene)acetate

There total 5 articles about 8a(R)-methyl (8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ylidene)acetate 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:

(2S)-2-phenylglycinol (20989-17-7) + 3,7-dioxo-octanoic acid methyl ester → methyl 3-methyl-1-oxo-2-cyclohexene-2-carboxylate (86891-79-4) + 8a(R)-methyl (8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ylidene)acetate (163813-49-8) + 8a(S)-methyl (8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ylidene)acetate

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 20 ℃; for 12h;

DOI:10.1021/jo049961c

Reference yield:

bromoacetic acid methyl ester (96-32-2) + (3S,8aR)-8a-Methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-thione → 8a(R)-methyl (8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ylidene)acetate (163813-49-8)

Guidance literature:

With triethylamine; phosphorous acid trimethyl ester; Yield given. Multistep reaction; 1.) CHCl₃, overnight, 2.) CHCl₃, reflux;

DOI:10.1021/ja00124a039

Reference yield:

7-methyl-3-oxo-methyl-oct-7-en-oate (71203-75-3) → 8a(R)-methyl (8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ylidene)acetate (163813-49-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: Me₂S / CH₂Cl₂ / 48 h / 20 °C

2.1: p-TsOH / benzene / 12 h / 20 °C

With toluene-4-sulfonic acid; ozone; In dichloromethane; benzene;

DOI:10.1021/jo049961c

upstream raw materials:

bromoacetic acid methyl ester

(2S)-2-phenylglycinol

7-methyl-3-oxo-methyl-oct-7-en-oate

7-oxo-hept-2-ynoic acid methyl ester

Downstream raw materials:

(5S,8aR)-(8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-acetic acid methyl ester