(S)-5-hydroxy-5-(2-phenethyl)-3-keto-6-methylheptanoic acid ethyl ester

Base Information

• Chemical Name: (S)-5-hydroxy-5-(2-phenethyl)-3-keto-6-methylheptanoic acid ethyl ester
• CAS No.: 260257-63-4
• Molecular Formula: C₁₈H₂₆O₄
• Molecular Weight: 306.402
• Mol file: 260257-63-4.mol

Synonyms:(S)-5-hydroxy-5-(2-phenethyl)-3-keto-6-methylheptanoic acid ethyl ester

Chemical Property of (S)-5-hydroxy-5-(2-phenethyl)-3-keto-6-methylheptanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-hydroxy-5-(2-phenethyl)-3-keto-6-methylheptanoic acid ethyl ester

There total 12 articles about (S)-5-hydroxy-5-(2-phenethyl)-3-keto-6-methylheptanoic acid ethyl 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:

3-methyl-butan-2-one (563-80-4) → (S)-5-hydroxy-5-(2-phenethyl)-3-keto-6-methylheptanoic acid ethyl ester (260257-63-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 80 percent / Ba(OH)2 / ethanol / 20 °C

2.1: 95 percent / H₂ / Raney Ni / tetrahydrofuran / 20 °C / 1292.87 Torr

3.1: i-Pr₂NH; n-BuLi / tetrahydrofuran / -40 - -15 °C

4.1: LiOH / methanol; H₂O / Heating

5.1: (R)-α-methylbenzylamine / ethyl acetate / Heating

5.2: 1N HCl

6.1: CDI / tetrahydrofuran / 4 h / 20 °C

6.2: 4.7 g / tetrahydrofuran / 20 °C

With barium dihydroxide; lithium hydroxide; n-butyllithium; (R)-1-phenyl-ethyl-amine; hydrogen; diisopropylamine; 1,1'-carbonyldiimidazole; nickel; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; 1.1: Condensation / 2.1: Hydrogenation / 3.1: Condensation / 4.1: Hydrolysis / 5.1: salt formation; chiral resolution / 5.2: chiral resolution / 6.1: Substitution / 6.2: Substitution;

DOI:10.1016/S0968-0896(99)00215-1

Reference yield:

p-benzyloxybenzaldehyde (4397-53-9) → (S)-5-hydroxy-5-(2-phenethyl)-3-keto-6-methylheptanoic acid ethyl ester (260257-63-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 80 percent / Ba(OH)2 / ethanol / 20 °C

2.1: 95 percent / H₂ / Raney Ni / tetrahydrofuran / 20 °C / 1292.87 Torr

3.1: i-Pr₂NH; n-BuLi / tetrahydrofuran / -40 - -15 °C

4.1: LiOH / methanol; H₂O / Heating

5.1: (R)-α-methylbenzylamine / ethyl acetate / Heating

5.2: 1N HCl

6.1: CDI / tetrahydrofuran / 4 h / 20 °C

6.2: 4.7 g / tetrahydrofuran / 20 °C

With barium dihydroxide; lithium hydroxide; n-butyllithium; (R)-1-phenyl-ethyl-amine; hydrogen; diisopropylamine; 1,1'-carbonyldiimidazole; nickel; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; 1.1: Condensation / 2.1: Hydrogenation / 3.1: Condensation / 4.1: Hydrolysis / 5.1: salt formation; chiral resolution / 5.2: chiral resolution / 6.1: Substitution / 6.2: Substitution;

DOI:10.1016/S0968-0896(99)00215-1

Reference yield:

1-(4-benzyloxyphenyl)-4-methylpent-1-ene-3-one → (S)-5-hydroxy-5-(2-phenethyl)-3-keto-6-methylheptanoic acid ethyl ester (260257-63-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / H₂ / Raney Ni / tetrahydrofuran / 20 °C / 1292.87 Torr

2.1: i-Pr₂NH; n-BuLi / tetrahydrofuran / -40 - -15 °C

3.1: LiOH / methanol; H₂O / Heating

4.1: (R)-α-methylbenzylamine / ethyl acetate / Heating

4.2: 1N HCl

5.1: CDI / tetrahydrofuran / 4 h / 20 °C

5.2: 4.7 g / tetrahydrofuran / 20 °C

With lithium hydroxide; n-butyllithium; (R)-1-phenyl-ethyl-amine; hydrogen; diisopropylamine; 1,1'-carbonyldiimidazole; nickel; In tetrahydrofuran; methanol; water; ethyl acetate; 1.1: Hydrogenation / 2.1: Condensation / 3.1: Hydrolysis / 4.1: salt formation; chiral resolution / 4.2: chiral resolution / 5.1: Substitution / 5.2: Substitution;

DOI:10.1016/S0968-0896(99)00215-1

upstream raw materials:

(S)-3-hydroxy-3-(2-phenethyl)-4-methylpentanoic acid

3-methyl-butan-2-one

p-benzyloxybenzaldehyde

3-<4-(benzyloxy)phenyl>-propanoyl chloride

Downstream raw materials:

(S)-4-hydroxy-6-isopropyl-6-(2-phenethyl)-5,6-dihydropyran-2-one