Benzyl-[(S)-4'a-methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-(5'E)-ylidene]-amine

Base Information

• Chemical Name: Benzyl-[(S)-4'a-methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-(5'E)-ylidene]-amine
• CAS No.: 119755-33-8
• Molecular Formula: C₂₀H₂₅NO₂
• Molecular Weight: 311.424

Synonyms:Benzyl-[(S)-4'a-methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-(5'E)-ylidene]-amine

Chemical Property of Benzyl-[(S)-4'a-methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-(5'E)-ylidene]-amine

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of Benzyl-[(S)-4'a-methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-(5'E)-ylidene]-amine

There total 3 articles about Benzyl-[(S)-4'a-methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-(5'E)-ylidene]-amine 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:

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione (33878-99-8) → Benzyl-[(S)-4'a-methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-(5'E)-ylidene]-amine (119755-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1: collidinium p-toluenesulfonate / benzene / Heating; 1.) 20 h; 2.) several days

2: p-toluenesulfonic acid / benzene / 24 h / Heating

collidinium p-toluene sulfonate; toluene-4-sulfonic acid; In benzene;

DOI:10.1021/ja00197a039

Reference yield:

4',4'a,6',7'-(+)-Tetrahydro-4'aS*-methylspiro<1,3-dioxolane-2,2'(1'H)-naphthalen>-5'(3'H)-one (32533-91-8,119772-90-6,143840-13-5) + benzylamine (100-46-9) → Benzyl-[(S)-4'a-methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-(5'E)-ylidene]-amine (119755-33-8)

Guidance literature:

toluene-4-sulfonic acid; In benzene; for 24h; Heating;

DOI:10.1021/ja00197a039

Reference yield:

(S)-4'a-Methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one (119772-90-6) + benzylamine (100-46-9) → Benzyl-[(S)-4'a-methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-(5'E)-ylidene]-amine (119755-33-8)

Guidance literature:

toluene-4-sulfonic acid; In benzene; for 24h; Heating;

DOI:10.1016/0040-4039(88)85209-2

upstream raw materials:

(S)-4'a-Methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one

benzylamine

4',4'a,6',7'-(+)-Tetrahydro-4'aS^*-methylspiro<1,3-dioxolane-2,2'(1'H)-naphthalen>-5'(3'H)-one

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Downstream raw materials:

<3aS-(3aα,9aα,9bβ)>-3,3a,4,5,8,9,9a,9b-Octahydro-9a,9b-dimethyl-6-<(phenylthio)methyl>-1H-benzindene-1,7(2H)-dione

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