(R)-5,6-dihydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one

Base Information

• Chemical Name: (R)-5,6-dihydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one
• CAS No.: 916489-11-7
• Molecular Formula: C₁₅H₁₄FNO₂
• Molecular Weight: 259.28
• Mol file: 916489-11-7.mol

Synonyms:(R)-5,6-dihydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one

Chemical Property of (R)-5,6-dihydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5,6-dihydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one

There total 2 articles about (R)-5,6-dihydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one 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: 70.0%

(R)-5-hydroxy-7-cyanohept-2-ynoic acid ethyl ester (916489-09-3) + (4-fluorobenzyl)magnesium chloride (1643-73-8) → (R)-5,6-dihydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one (916489-11-7)

Guidance literature:

(4-fluorobenzyl)magnesium chloride; With lithium chloride; In tetrahydrofuran; at -30 - -20 ℃; for 1.16667h;

(R)-5-hydroxy-7-cyanohept-2-ynoic acid ethyl ester; In tetrahydrofuran; at -5 ℃;

With methanol; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo0616963

Reference yield:

1-chloromethyl-4-fluorobenzene (352-11-4) → (R)-5,6-dihydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one (916489-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Mg / tetrahydrofuran / 2.17 h

2.1: CuCN; LiCl / tetrahydrofuran / 1.17 h / -30 - -20 °C

2.2: tetrahydrofuran / -5 °C

2.3: 70 percent / MeOH / tetrahydrofuran / 0 - 20 °C

With magnesium; lithium chloride; In tetrahydrofuran;

DOI:10.1021/jo0616963

Reference yield: 82.0%

(R)-5,6-dihydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one (916489-11-7) → (4S,6R)-tetrahydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one (916489-16-2)

Guidance literature:

With hydrogen; Pt/Al₂O₃; In tetrahydrofuran; at 20 ℃; for 24h; under 2585.74 Torr;

DOI:10.1021/jo0616963

upstream raw materials:

(R)-5-hydroxy-7-cyanohept-2-ynoic acid ethyl ester

(4-fluorobenzyl)magnesium chloride

1-chloromethyl-4-fluorobenzene

Downstream raw materials:

(4S,6R)-tetrahydro-6-(2-cyanoethyl)-4-(4-fluorobenzyl)-2H-pyran-2-one

(2S,4R)-1-propyl-2-(2-cyanoethyl)-4-(4-fluorobenzyl)piperidine

(2S,4R)-1-propyl-2-(3-aminopropyl)-4-(4-fluorobenzyl)piperidine