(1S,2S)-1-(4-fluorobenzamido)-7-(4-(oxetan-3-yl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl methylcarbamate

Base Information

• Chemical Name: (1S,2S)-1-(4-fluorobenzamido)-7-(4-(oxetan-3-yl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl methylcarbamate
• CAS No.: 1373215-17-8
• Molecular Formula: C₂₆H₃₁FN₄O₄
• Molecular Weight: 482.555
• Mol file: 1373215-17-8.mol

Synonyms:(1S,2S)-1-(4-fluorobenzamido)-7-(4-(oxetan-3-yl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl methylcarbamate

Chemical Property of (1S,2S)-1-(4-fluorobenzamido)-7-(4-(oxetan-3-yl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl methylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-1-(4-fluorobenzamido)-7-(4-(oxetan-3-yl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl methylcarbamate

There total 10 articles about (1S,2S)-1-(4-fluorobenzamido)-7-(4-(oxetan-3-yl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl methylcarbamate 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: 75.0%

4-fluoro-N-((1S,2S)-2-hydroxy-7-(4-(oxetan-3-yl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide + 1,1'-carbonyldiimidazole (530-62-1) + methylamine (74-89-5) → (1S,2S)-1-(4-fluorobenzamido)-7-(4-(oxetan-3-yl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl methylcarbamate (1373215-17-8)

Guidance literature:

4-fluoro-N-((1S,2S)-2-hydroxy-7-(4-(oxetan-3-yl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide; 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 8h;

methylamine; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1021/ml500283g

Reference yield:

(1S,2S)-1-amino-7-bromo-1,2,3,4-tetrahydronaphthalen-2-ol (2S,3S)-2,3-bis(4-methylbenzoyloxy)succinate (1373215-27-0) → (1S,2S)-1-(4-fluorobenzamido)-7-(4-(oxetan-3-yl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl methylcarbamate (1373215-17-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydrogencarbonate / water; tetrahydrofuran / 1 h / 0 - 5 °C

2.1: potassium carbonate; copper(l) iodide; N,N`-dimethylethylenediamine / toluene / 17 h / 110 °C / Inert atmosphere

3.1: borane-dimethyl sulfide complex / tetrahydrofuran / 1 h / 0 - 20 °C

4.1: hydrogenchloride / 1,4-dioxane / 13 h / 20 - 50 °C

5.1: sodium tris(acetoxy)borohydride / acetonitrile / 7 h / 20 °C

6.1: tetrahydrofuran / 8 h / 20 °C

6.2: 0.25 h / 20 °C

With hydrogenchloride; copper(l) iodide; borane-dimethyl sulfide complex; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; potassium carbonate; N,N`-dimethylethylenediamine; In tetrahydrofuran; 1,4-dioxane; water; toluene; acetonitrile;

DOI:10.1021/ml500283g

Reference yield:

4-fluoro-N-((1S,2S)-2-hydroxy-7-(piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide hydrochloride (1373215-41-8) → (1S,2S)-1-(4-fluorobenzamido)-7-(4-(oxetan-3-yl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl methylcarbamate (1373215-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium tris(acetoxy)borohydride / acetonitrile / 7 h / 20 °C

2.1: tetrahydrofuran / 8 h / 20 °C

2.2: 0.25 h / 20 °C

With sodium tris(acetoxy)borohydride; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ml500283g

upstream raw materials:

bromo-7 dihydro-3,4 naphthalene

(1S,2S)-1-amino-7-bromo-1,2,3,4-tetrahydronaphthalen-2-ol (2S,3S)-2,3-bis(4-methylbenzoyloxy)succinate

N-((1S,2S)-7-bromo-2-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)-4-fluorobenzamide

tert-butyl 4-((7S,8S)-8-(4-fluorobenzamido)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-3-oxopiperazine-1-carboxylate