(4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-c]isoxazole

Base Information

• Chemical Name: (4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-c]isoxazole
• CAS No.: 1207384-24-4
• Molecular Formula: C₂₀H₂₅NO₂
• Molecular Weight: 311.424

Synonyms:

Chemical Property of (4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-c]isoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-c]isoxazole

There total 10 articles about (4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-c]isoxazole 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:

C20H26O3 → (4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-c]isoxazole (1207384-24-4) + (4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-d]isoxazole (1207384-23-3)

Guidance literature:

With hydroxylamine hydrochloride; In ethanol; water; for 1.5h; Reflux;

DOI:10.1021/ol902711b

Reference yield:

(+)-7-epi-α-cyperone (547-26-2) → (4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-c]isoxazole (1207384-24-4) + (4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-d]isoxazole (1207384-23-3)

Guidance literature:

Multi-step reaction with 9 steps

1: tert-butyl alcohol; lithium; ammonia / hexane; tetrahydrofuran / 2 h / -33 °C / Inert atmosphere

2: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0 °C / Reflux; Inert atmosphere

3: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 20 °C / Inert atmosphere

4: sodium periodate / water; ethanol / 1 h / 20 °C / Inert atmosphere

5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 32 h / 20 °C / Inert atmosphere

6: potassium carbonate / methanol / 20 °C / Inert atmosphere

7: dipyridinium dichromate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

8: sodium hydride / diethyl ether / 5 h / 20 °C / Inert atmosphere

9: hydroxylamine hydrochloride / water; ethanol / 1.5 h / Inert atmosphere; Reflux

With sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; hydroxylamine hydrochloride; ammonia; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; tert-butyl alcohol; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1: |Birch Reduction / 5: |Baeyer-Villiger Ketone Oxidation;

DOI:10.1021/jo501122k

Reference yield:

(4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyloctahydronaphthalen-2(1H)-one → (4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-c]isoxazole (1207384-24-4) + (4aR,7S,8S,8aS)-7-(benzyloxy)-4a,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-d]isoxazole (1207384-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / diethyl ether / 5 h / 20 °C / Inert atmosphere

2: hydroxylamine hydrochloride / water; ethanol / 1.5 h / Inert atmosphere; Reflux

With hydroxylamine hydrochloride; sodium hydride; In diethyl ether; ethanol; water;

DOI:10.1021/jo501122k

upstream raw materials:

(+)-7-epi-α-cyperone

(1S,2S,4aS,7S,8aS)-1,4a-dimethyl-7-(prop-1-en-2-yl)decahydronaphthalen-2-ol

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