(6R,7aR)-3-(cyclohexylideneamino)-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one

Base Information

Chemical Name:(6R,7aR)-3-(cyclohexylideneamino)-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one
CAS No.:1174133-89-1
Molecular Formula:C₁₆H₂₄N₂O₂
Molecular Weight:276.379
Hs Code.:

Synonyms:(6R,7aR)-3-(cyclohexylideneamino)-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one

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Chemical Property of (6R,7aR)-3-(cyclohexylideneamino)-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one

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Technology Process of (6R,7aR)-3-(cyclohexylideneamino)-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one

There total 6 articles about (6R,7aR)-3-(cyclohexylideneamino)-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one 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%

: 1051911-43-3
(3aS,6R,7aR)-3-amino-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one

: 108-94-1,11119-77-0,9003-41-2,9075-99-4
cyclohexanone

: 1174133-89-1
(6R,7aR)-3-(cyclohexylideneamino)-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; for 14h;
DOI:10.1021/acs.joc.8b00655

Reference yield:

: 3144-16-9,61380-66-3
(1S)-10-camphorsulfonic acid

: 1174133-89-1
(6R,7aR)-3-(cyclohexylideneamino)-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: thionyl chloride / 0.5 h / Reflux

2.1: sodium carbonate; potassium permanganate / acetonitrile; water / 1.5 h / 20 - 70 °C

3.1: thionyl chloride; pyridine / 2 h / Reflux

4.1: sodium azide / water; acetone / 3 h / 20 °C

5.1: cerium(III) chloride heptahydrate / methanol / 0.17 h / 0 °C

5.2: 2.5 h / -78 - -40 °C

6.1: potassium tert-butylate / tetrahydrofuran / 3.5 h / 20 °C

6.2: 3 h

7.1: toluene-4-sulfonic acid / dichloromethane / 14 h

With pyridine; potassium permanganate; thionyl chloride; sodium azide; cerium(III) chloride heptahydrate; potassium tert-butylate; sodium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile;
DOI:10.1021/acs.joc.8b00655

Reference yield:

: 54371-12-9,66884-33-1,66965-39-7,86023-72-5
ketopinic acid chloride

: 1174133-89-1
(6R,7aR)-3-(cyclohexylideneamino)-8,8-dimethylhexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium azide / water; acetone / 3 h / 20 °C

2.1: cerium(III) chloride heptahydrate / methanol / 0.17 h / 0 °C

2.2: 2.5 h / -78 - -40 °C

3.1: potassium tert-butylate / tetrahydrofuran / 3.5 h / 20 °C

3.2: 3 h

4.1: toluene-4-sulfonic acid / dichloromethane / 14 h

With sodium azide; cerium(III) chloride heptahydrate; potassium tert-butylate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1021/acs.joc.8b00655