{(S)-2-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-1-naphthalen-1-yl-ethyl}-carbamic acid methyl ester

Base Information

• Chemical Name: {(S)-2-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-1-naphthalen-1-yl-ethyl}-carbamic acid methyl ester
• CAS No.: 750594-63-9
• Molecular Formula: C₂₄H₃₁NO₂
• Molecular Weight: 365.516
• Mol file: 750594-63-9.mol

Synonyms:{(S)-2-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-1-naphthalen-1-yl-ethyl}-carbamic acid methyl ester

Chemical Property of {(S)-2-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-1-naphthalen-1-yl-ethyl}-carbamic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(S)-2-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-1-naphthalen-1-yl-ethyl}-carbamic acid methyl ester

There total 5 articles about {(S)-2-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-1-naphthalen-1-yl-ethyl}-carbamic acid methyl ester 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: 83.0%

sodium methylate (124-41-4) + (S)-3-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-2-naphthalen-1-yl-propionic acid (750594-62-8) → {(S)-2-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-1-naphthalen-1-yl-ethyl}-carbamic acid methyl ester (750594-63-9)

Guidance literature:

(S)-3-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-2-naphthalen-1-yl-propionic acid; With diphenyl-phosphinic acid; triethylamine; In toluene; for 1h; Heating;

sodium methylate; In methanol; toluene; for 1h; Heating;

DOI:10.1021/ol048936q

Reference yield:

(S)-3-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-2-naphthalen-1-yl-propan-1-ol (750594-61-7) → {(S)-2-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-1-naphthalen-1-yl-ethyl}-carbamic acid methyl ester (750594-63-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 53 percent / Jones reagent / acetone / 2 h / 0 °C

2.1: DPPA; Et₃N / toluene / 1 h / Heating

2.2: 83 percent / toluene; methanol / 1 h / Heating

With jones reagent; diphenyl-phosphinic acid; triethylamine; In acetone; toluene; 2.1: Curtius rearrangement;

DOI:10.1021/ol048936q

Reference yield:

(1R,2S,5R)-1-[(E)-3-(tert-Butyl-diphenyl-silanyloxy)-propenyl]-2-isopropyl-5-methyl-cyclohexanol (750594-47-9) → {(S)-2-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-1-naphthalen-1-yl-ethyl}-carbamic acid methyl ester (750594-63-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

1.2: tetrahydrofuran; hexane / 2 h / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: CuCN / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.3: 1.50 g / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

3.1: 98 percent / TBAF / tetrahydrofuran / 15 h / 20 °C

4.1: 53 percent / Jones reagent / acetone / 2 h / 0 °C

5.1: DPPA; Et₃N / toluene / 1 h / Heating

5.2: 83 percent / toluene; methanol / 1 h / Heating

With n-butyllithium; jones reagent; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; hexane; acetone; toluene; 5.1: Curtius rearrangement;

DOI:10.1021/ol048936q

upstream raw materials:

sodium methylate

(S)-3-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-2-naphthalen-1-yl-propionic acid

(S)-3-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-2-naphthalen-1-yl-propan-1-ol

(1R,2S,5R)-1-[(E)-3-(tert-Butyl-diphenyl-silanyloxy)-propenyl]-2-isopropyl-5-methyl-cyclohexanol