(-)-(5S)-2,3,6,7,8,8a-hexahydro-5-pentyl-3-phenyl-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile

Base Information

• Chemical Name: (-)-(5S)-2,3,6,7,8,8a-hexahydro-5-pentyl-3-phenyl-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
• CAS No.: 159638-92-3
• Molecular Formula: C₁₉H₂₆N₂O
• Molecular Weight: 298.428

Synonyms:(-)-(5S)-2,3,6,7,8,8a-hexahydro-5-pentyl-3-phenyl-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile

Chemical Property of (-)-(5S)-2,3,6,7,8,8a-hexahydro-5-pentyl-3-phenyl-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile

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Technology Process of (-)-(5S)-2,3,6,7,8,8a-hexahydro-5-pentyl-3-phenyl-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile

There total 1 articles about (-)-(5S)-2,3,6,7,8,8a-hexahydro-5-pentyl-3-phenyl-5H-[1,3]oxazolo[3,2-a]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: 85.0%

1-Bromopentane (110-53-2) + (-)-2-cyano-6-phenyloxazolopiperidine (88056-92-2) → (-)-(5S)-2,3,6,7,8,8a-hexahydro-5-pentyl-3-phenyl-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile (159638-92-3)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1002/1099-0690(200006)2000:11<2057::AID-EJOC2057>3.0.CO;2-F

Reference yield: 93.0%

(-)-(5S)-2,3,6,7,8,8a-hexahydro-5-pentyl-3-phenyl-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile (159638-92-3) → (-)-(2S)-2-pentyl-1-(1-phenyl-2-hydroxyethyl)piperidine (289039-58-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 2h; Heating;

DOI:10.1002/1099-0690(200006)2000:11<2057::AID-EJOC2057>3.0.CO;2-F

Reference yield: 77.0%

(-)-(5S)-2,3,6,7,8,8a-hexahydro-5-pentyl-3-phenyl-5H-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile (159638-92-3) → (-)-(5S)-5-pentyl-3-phenyloctahydropyrido[2,1-b]oxazole (289039-68-5)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1002/1099-0690(200006)2000:11<2057::AID-EJOC2057>3.0.CO;2-F

upstream raw materials:

1-Bromopentane

(-)-2-cyano-6-phenyloxazolopiperidine

Downstream raw materials:

(-)-(5S)-5-pentyl-3-phenyloctahydropyrido[2,1-b]oxazole

(-)-(2S)-2-pentyl-1-(1-phenyl-2-hydroxyethyl)piperidine

(+)-(2S)-2-pentylpiperidine

(+)-(2S,6S)-2-[(methoxycarbonyl)methyl]-6-pentyl-1-(1-phenyl-2-hydroxyethyl)piperidine

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