(3R)-3-(4-fluorophenyl)-5-hydroxypentanoic acid (1S)-1-phenylethylamide

Base Information

• Chemical Name: (3R)-3-(4-fluorophenyl)-5-hydroxypentanoic acid (1S)-1-phenylethylamide
• CAS No.: 349446-92-0
• Molecular Formula: C₁₉H₂₂FNO₂
• Molecular Weight: 315.388
• Mol file: 349446-92-0.mol

Synonyms:(3R)-3-(4-fluorophenyl)-5-hydroxypentanoic acid (1S)-1-phenylethylamide

Chemical Property of (3R)-3-(4-fluorophenyl)-5-hydroxypentanoic acid (1S)-1-phenylethylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-3-(4-fluorophenyl)-5-hydroxypentanoic acid (1S)-1-phenylethylamide

There total 7 articles about (3R)-3-(4-fluorophenyl)-5-hydroxypentanoic acid (1S)-1-phenylethylamide 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:

4-(4-fluorophenyl)dihydropyran-2,6(3H)-dione (4926-12-9) → (3R)-3-(4-fluorophenyl)-5-hydroxypentanoic acid (1S)-1-phenylethylamide (349446-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃N / toluene / -78 - 20 °C

2.1: Et₃N / tetrahydrofuran / 1 h / 20 °C

2.2: -78 - 20 °C

3.1: 4.3 g / sodium borohydride; H₂O / tetrahydrofuran

With sodium tetrahydroborate; water; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1016/S0957-4166(01)00069-6

Reference yield:

4-fluorocinnamic acid (459-32-5,14290-66-5,14290-86-9) → (3R)-3-(4-fluorophenyl)-5-hydroxypentanoic acid (1S)-1-phenylethylamide (349446-92-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 99 percent / thionyl chloride / 18 h / 20 °C

2.1: Na; MeOH / 0.5 h

2.2: 67 percent / methanol / 20 h / Heating

3.1: aq. NaOH / 20 h / Heating

4.1: 15.5 g / aq. HCl / 20 h / Heating

5.1: 90 percent / acetyl chloride / 20 h / Heating

6.1: Et₃N / toluene / -78 - 20 °C

7.1: Et₃N / tetrahydrofuran / 1 h / 20 °C

7.2: -78 - 20 °C

8.1: 4.3 g / sodium borohydride; H₂O / tetrahydrofuran

With hydrogenchloride; methanol; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; water; sodium; triethylamine; acetyl chloride; In tetrahydrofuran; toluene; 2.2: Michael addition;

DOI:10.1016/S0957-4166(01)00069-6

Reference yield:

3-(4-fluorophenyl)pentan-1,5-dioic acid (3449-63-6) → (3R)-3-(4-fluorophenyl)-5-hydroxypentanoic acid (1S)-1-phenylethylamide (349446-92-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / acetyl chloride / 20 h / Heating

2.1: Et₃N / toluene / -78 - 20 °C

3.1: Et₃N / tetrahydrofuran / 1 h / 20 °C

3.2: -78 - 20 °C

4.1: 4.3 g / sodium borohydride; H₂O / tetrahydrofuran

With sodium tetrahydroborate; water; triethylamine; acetyl chloride; In tetrahydrofuran; toluene;

DOI:10.1016/S0957-4166(01)00069-6

upstream raw materials:

4-(4-fluorophenyl)dihydropyran-2,6(3H)-dione

4-fluorocinnamic acid

3-(4-fluorophenyl)pentan-1,5-dioic acid

methyl p-fluorocinnamate

Downstream raw materials:

Methanesulfonic acid (3S,4R)-4-(4-fluoro-phenyl)-1-((S)-1-phenyl-ethyl)-piperidin-3-ylmethyl ester

(3S,4R,1'S)-4-(4-fluorophenyl)-3-methoxycarbonyl-1-(1'-phenylethyl)piperidin-2-one

{(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine

(4R,1'S)-4-(4-fluorophenyl)-1-(1'-phenylethyl)piperidin-2-one