(2R,3R)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone

Base Information

• Chemical Name: (2R,3R)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone
• CAS No.: 107148-88-9
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.268
• Mol file: 107148-88-9.mol

Synonyms:(2R,3R)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone

Chemical Property of (2R,3R)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone

There total 1 articles about (2R,3R)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone 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:

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) + (2R)-(-)-1-(triphenylmethoxy)-2-<(methylsulfonyl)oxy>propane (107148-84-5) → (2R,3R)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone (107148-88-9)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/jo00383a026

Reference yield:

(2RS,3S)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone (107148-85-6,107148-86-7,107148-87-8,107148-88-9) → (S)-verapamil (36622-29-4,56949-77-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, 45 deg C, 4 h, 2.) THF, from 0 deg C to RT, 14 h

2: 95 percent / NH₃, AlMe₃ / 1,1,2-trichloro-ethane; toluene / 60 h / Heating

3: 96 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: 93 percent / NaBH₄, tert-butyl alcohol / CH₂Cl₂ / 70 h / Heating

5: 1.) borane, 2-methyl-2-butene, 2.) 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF, H₂O, 0 deg C, 30 min

6: Et₃N / CH₂Cl₂ / 24 h / 0 °C

7: Et₃N / tetrahydrofuran / 48 h / 80 °C

With sodium tetrahydroborate; 2-methyl-but-2-ene; borane; ammonia; dihydrogen peroxide; trimethylaluminum; sodium hydride; triethylamine; tert-butyl alcohol; In tetrahydrofuran; dichloromethane; 1,1,2-trichloroethane; toluene;

DOI:10.1021/jo00383a026

Reference yield:

(2R,3R)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone (107148-88-9) → (S)-verapamil (36622-29-4,56949-77-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, 45 deg C, 4 h, 2.) THF, for 0 deg C to RT, 14 h

2: 94 percent / NH₃, AlMe₃ / 1,1,2-trichloro-ethane; toluene / 60 h / Heating

3: 97 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: 93 percent / NaBH₄, tert-butyl alcohol / CH₂Cl₂ / 70 h / Heating

5: 1.) borane, 2-methyl-2-butene, 2.) 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF, H₂O, 0 deg C, 30 min

6: Et₃N / CH₂Cl₂ / 24 h / 0 °C

7: Et₃N / tetrahydrofuran / 48 h / 80 °C

With sodium tetrahydroborate; 2-methyl-but-2-ene; borane; ammonia; dihydrogen peroxide; trimethylaluminum; sodium hydride; triethylamine; tert-butyl alcohol; In tetrahydrofuran; dichloromethane; 1,1,2-trichloroethane; toluene;

DOI:10.1021/jo00383a026

upstream raw materials:

(3,4-Dimethoxyphenyl)acetic acid

(2R)-(-)-1-(triphenylmethoxy)-2-<(methylsulfonyl)oxy>propane

Downstream raw materials:

(2S,3S)-(-)-2-(2-propenyl)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone

(4S)-(+)-4-cyano-4-(3,4-dimethoxyphenyl)-4-isopropylbutene

(2S)-(-)-2-(3,4-dimethoxyphenyl)-5-hydroxy-2-isopropylpentanenitrile

(2S,3S)-(+)-2-methyl-3-cyano-3-(3,4-dimethoxyphenyl)hex-5-enol