7,8-dihydro-3-phenyl-3R-[3α,8aα]-5H-oxazolo[3,2a]pyridine-5-carbonitrile

Base Information

• Chemical Name: 7,8-dihydro-3-phenyl-3R-[3α,8aα]-5H-oxazolo[3,2a]pyridine-5-carbonitrile
• CAS No.: 277755-26-7
• Molecular Formula: C₁₄H₁₄N₂O
• Molecular Weight: 226.278

Synonyms:7,8-dihydro-3-phenyl-3R-[3α,8aα]-5H-oxazolo[3,2a]pyridine-5-carbonitrile

Chemical Property of 7,8-dihydro-3-phenyl-3R-[3α,8aα]-5H-oxazolo[3,2a]pyridine-5-carbonitrile

Chemical Property:

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Technology Process of 7,8-dihydro-3-phenyl-3R-[3α,8aα]-5H-oxazolo[3,2a]pyridine-5-carbonitrile

There total 2 articles about 7,8-dihydro-3-phenyl-3R-[3α,8aα]-5H-oxazolo[3,2a]pyridine-5-carbonitrile 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: 35.0%

(3R,8aR)-3-Phenyl-hexahydro-oxazolo[3,2-a]pyridine-5,5-dicarbonitrile (277755-25-6) → 7,8-dihydro-3-phenyl-3R-[3α,8aα]-5H-oxazolo[3,2a]pyridine-5-carbonitrile (277755-26-7) + 7,8-dihydro-3-phenyl-3R-[3α,8aβ]-5H-oxazolo[3,2a]pyridine-5-carbonitrile

Guidance literature:

at 170 - 190 ℃; for 5h; under 20 Torr;

DOI:10.1021/jo990706f

Reference yield:

(-)-2-cyano-6-phenyloxazolopiperidine (88056-92-2) → 7,8-dihydro-3-phenyl-3R-[3α,8aα]-5H-oxazolo[3,2a]pyridine-5-carbonitrile (277755-26-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / LDA / tetrahydrofuran; hexane / 4 h / -78 °C

2: 35 percent / 5 h / 170 - 190 °C / 20 Torr

With lithium diisopropyl amide; In tetrahydrofuran; hexane; 1: Substitution / 2: Elimination;

DOI:10.1021/jo990706f

Reference yield: 82.0%

acetylenedicarboxylic acid diethyl ester (762-21-0) + 7,8-dihydro-3-phenyl-3R-[3α,8aα]-5H-oxazolo[3,2a]pyridine-5-carbonitrile (277755-26-7) → (5E,7E)-(3R,10aS)-5-Cyano-3-phenyl-2,3,10,10a-tetrahydro-9H-oxazolo[3,2-a]azocine-6,7-dicarboxylic acid diethyl ester

Guidance literature:

In dimethyl sulfoxide; at 110 ℃; for 0.5h;

DOI:10.1021/jo990706f

upstream raw materials:

(3R,8aR)-3-Phenyl-hexahydro-oxazolo[3,2-a]pyridine-5,5-dicarbonitrile

(-)-2-cyano-6-phenyloxazolopiperidine

Downstream raw materials:

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

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