(3S,6R,8aR)-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetic acid

Base Information

• Chemical Name: (3S,6R,8aR)-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetic acid
• CAS No.: 943739-63-7
• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.358
• Mol file: 943739-63-7.mol

Synonyms:(3S,6R,8aR)-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetic acid

Chemical Property of (3S,6R,8aR)-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6R,8aR)-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetic acid

There total 1 articles about (3S,6R,8aR)-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetic acid 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: 94.0%

6-allyl-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (943739-89-7) → (3S,6R,8aR)-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetic acid (943739-63-7)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 24h;

DOI:10.1021/jo070397q

Reference yield: 88.0%

(3S,6R,8aR)-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetic acid (943739-63-7) → (3R)-3-ethyl-3-(2-hydroxyethyl)-1-[(1S)-2-hydroxy-1-phenylethyl]piperidine (943739-66-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 28h;

DOI:10.1021/jo070397q

Reference yield:

(3S,6R,8aR)-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine-6-acetic acid (943739-63-7) → quebrachamine (4850-21-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / LiAlH₄ / tetrahydrofuran / 28 h / 20 °C

2: 69 percent / H₂ / Pd(OH)2/C / ethanol / 65 h / 20 °C / atmospheric pressure

3: pyridinium dichromate / dimethylformamide / 24 h / 20 °C

4: 70 mg / chlorotrimethylsilane / 24 h / 20 °C

5: 86 percent / tetrahydrofuran / 72 h / 20 °C

6: 74 percent / aqueous NaOH / methanol / 2.5 h / Heating

7: 85 percent / polyphosphoric acid / 0.5 h / 90 °C

8: 30 percent / LiAlH₄ / various solvent(s) / 7 h / Heating

With sodium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; chloro-trimethyl-silane; PPA; hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo070397q

upstream raw materials:

6-allyl-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Downstream raw materials:

(3R)-3-ethyl-3-(2-hydroxyethyl)-1-[(1S)-2-hydroxy-1-phenylethyl]piperidine

quebrachamine