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

Base Information

• Chemical Name: (3R,8R,8aR)-8-isopropyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
• CAS No.: 1572245-75-0
• Molecular Formula: C₁₆H₂₁NO₂
• Molecular Weight: 259.348

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

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

Chemical Property:

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

There total 2 articles about (3R,8R,8aR)-8-isopropyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 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: 73.0%

methyl 4-isopropyl-5-oxopentanoate (70687-49-9) + D-2-phenylglycinol (56613-80-0) → (3R,8S,8aS)-8-isopropyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1572245-84-1) + (3R,8R,8aR)-8-isopropyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1572245-75-0)

Guidance literature:

With sodium sulfate; In diethyl ether; at 0 ℃; for 5h; Solvent; Temperature; Time; Reagent/catalyst;

DOI:10.1021/jo5002627

Reference yield:

isovaleraldehyde (590-86-3) → (3R,8R,8aR)-8-isopropyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1572245-75-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: piperidine; potassium carbonate / 18 h / 0 - 20 °C

1.2: 0 °C / Reflux

1.3: Reflux

2.1: sodium sulfate / diethyl ether / 5 h / 0 °C

With piperidine; potassium carbonate; sodium sulfate; In diethyl ether;

DOI:10.1021/jo5002627

Reference yield: 71.0%

(3R,8R,8aR)-8-isopropyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1572245-75-0) → (S)-4-ethyl-5-{[(1R)-2-hydroxy-1-phenylethyl]amino}-1-pentanol (1572246-16-2) + (S)-[(R)-2-hydroxy-1-phenylethyl]-3-isopropylpiperidine (1572246-27-5)

Guidance literature:

With n-butyllithium; borane-ammonia complex; In tetrahydrofuran; hexane; at 0 - 40 ℃; for 1h;

DOI:10.1021/jo5002627

upstream raw materials:

methyl 4-isopropyl-5-oxopentanoate

D-2-phenylglycinol

isovaleraldehyde

Downstream raw materials:

(S)-4-ethyl-5-{[(1R)-2-hydroxy-1-phenylethyl]amino}-1-pentanol

(S)-[(R)-2-hydroxy-1-phenylethyl]-3-isopropylpiperidine

(S)-4-ethyl-5-[(2-nitrobenzenesulfonyl)amino]-1-pentanol

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