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

Base Information

• Chemical Name: tert-butyl 4-((7S,8S)-8-(4-fluorobenzamido)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)piperazine-1-carboxylate
• CAS No.: 1373215-40-7
• Molecular Formula: C₂₆H₃₂FN₃O₄
• Molecular Weight: 469.556
• Mol file: 1373215-40-7.mol

Synonyms:tert-butyl 4-((7S,8S)-8-(4-fluorobenzamido)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)piperazine-1-carboxylate

Chemical Property of tert-butyl 4-((7S,8S)-8-(4-fluorobenzamido)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)piperazine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-((7S,8S)-8-(4-fluorobenzamido)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)piperazine-1-carboxylate

There total 7 articles about tert-butyl 4-((7S,8S)-8-(4-fluorobenzamido)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)piperazine-1-carboxylate 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: 64.0%

tert-butyl 4-((7S,8S)-8-(4-fluorobenzamido)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-3-oxopiperazine-1-carboxylate (1373215-38-3) → tert-butyl 4-((7S,8S)-8-(4-fluorobenzamido)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)piperazine-1-carboxylate (1373215-40-7)

Guidance literature:

With borane-dimethyl sulfide complex; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

DOI:10.1021/ml500283g

Reference yield:

(+/-)-trans-1-amino-7-bromo-1,2,3,4-tetrahydronaphthalen-2-ol → tert-butyl 4-((7S,8S)-8-(4-fluorobenzamido)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)piperazine-1-carboxylate (1373215-40-7)

Guidance literature:

Multi-step reaction with 4 steps

1: water; acetonitrile / 0.5 h / 77 °C / Inert atmosphere; Resolution of racemate

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

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

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

With copper(l) iodide; borane-dimethyl sulfide complex; sodium hydrogencarbonate; potassium carbonate; N,N`-dimethylethylenediamine; In tetrahydrofuran; water; toluene; acetonitrile;

DOI:10.1021/ml500283g

Reference yield:

N-((1S,2S)-7-bromo-2-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)-4-fluorobenzamide (1373215-33-8) → tert-butyl 4-((7S,8S)-8-(4-fluorobenzamido)-7-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)piperazine-1-carboxylate (1373215-40-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With copper(l) iodide; borane-dimethyl sulfide complex; potassium carbonate; N,N`-dimethylethylenediamine; In tetrahydrofuran; toluene;

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

Downstream raw materials:

4-fluoro-N-((1S,2S)-2-hydroxy-7-(piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)benzamide hydrochloride

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