(1S^*,5R^*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-α,α-dichloro-N-methylacetamide

Base Information

• Chemical Name: (1S^*,5R^*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-α,α-dichloro-N-methylacetamide
• CAS No.: 125032-08-8
• Molecular Formula: C₂₄H₂₇Cl₂NO₄
• Molecular Weight: 464.389

Synonyms:(1S^*,5R^*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-α,α-dichloro-N-methylacetamide

Chemical Property of (1S^*,5R^*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-α,α-dichloro-N-methylacetamide

Chemical Property:

Purity/Quality:

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Technology Process of (1S^*,5R^*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-α,α-dichloro-N-methylacetamide

There total 8 articles about (1S^*,5R^*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-α,α-dichloro-N-methylacetamide 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: 80.0%

(1S*,2R*,5R*)-N-<5-(benzyloxy)-2-hydroxy-2-(3,4-dimethoxyphenyl)cyclohex-1-yl>-α,α-dichloro-N-methylacetamide (125032-07-7) → N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-1-en-1-yl>-α,α-dichloro-N-methylacetamide (125032-09-9) + (1S*,5R*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-α,α-dichloro-N-methylacetamide (125032-08-8)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 1h; Heating;

DOI:10.1021/jo00001a021

Reference yield: 79.0%

dichloroacethyl chloride (79-36-7) + (1R*,2S*,4R*)-4-(benzyloxy)-1-(3,4-dimethoxyphenyl)-2-(methylamino)cyclohexan-1-ol (125032-06-6) → (1S*,5R*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-α,α-dichloro-N-methylacetamide (125032-08-8) + (1S*,2R*,5R*)-N-<5-(benzyloxy)-2-hydroxy-2-(3,4-dimethoxyphenyl)cyclohex-1-yl>-α,α-dichloro-N-methylacetamide (125032-07-7)

Guidance literature:

With triethylamine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00001a021

Reference yield:

4-(benzyloxy)-1-(3,4-dimethoxyphenyl)cyclohex-1-ene (82732-16-9) → (1S*,5R*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-α,α-dichloro-N-methylacetamide (125032-08-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 10 percent / N-bromosuccinimide / acetonitrile; H₂O

2: 83 percent / methanol / 100 °C / in a sealed tube

3: 8 percent / NEt₃ / CH₂Cl₂

With N-Bromosuccinimide; triethylamine; In methanol; dichloromethane; water; acetonitrile;

DOI:10.1039/c39890000762

upstream raw materials:

dichloroacethyl chloride

(1R^*,2S^*,4R^*)-4-(benzyloxy)-1-(3,4-dimethoxyphenyl)-2-(methylamino)cyclohexan-1-ol

(1S^*,2R^*,5R^*)-N-<5-(benzyloxy)-2-hydroxy-2-(3,4-dimethoxyphenyl)cyclohex-1-yl>-α,α-dichloro-N-methylacetamide

4-(benzyloxy)-1-(3,4-dimethoxyphenyl)cyclohex-1-ene

Downstream raw materials:

(3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindol-2-one

(1S^*,5R^*)-N-<5-(benzyloxy)-2-(3,4-dimethoxyphenyl)cyclohex-2-en-1-yl>-N-methylacetamide

(3aR^*,6R^*,7aS^*)-6-(benzyloxy)octahydro-3a-(3,4-dimethoxyphenyl)-1-methylindole

(+/-)-mesembranol

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