(S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (R)-1-(3-tert-butoxycarbonylmethoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-propyl ester

Base Information

• Chemical Name: (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (R)-1-(3-tert-butoxycarbonylmethoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-propyl ester
• CAS No.: 215169-04-3
• Molecular Formula: C₃₅H₄₇NO₉
• Molecular Weight: 625.759
• Mol file: 215169-04-3.mol

Synonyms:(S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (R)-1-(3-tert-butoxycarbonylmethoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-propyl ester

Chemical Property of (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (R)-1-(3-tert-butoxycarbonylmethoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (R)-1-(3-tert-butoxycarbonylmethoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-propyl ester

There total 7 articles about (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (R)-1-(3-tert-butoxycarbonylmethoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-propyl 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: 72.0%

(2S)-1-(1,2-dioxo-3 3-dimethylpentyl)-2-pyrrolidinecarboxylic acid (186268-78-0) + (R)-1-(3-(tert-butoxycarbonylmethoxy)phenyl)-3-(3,4-dimethoxyphenyl)-propan-1-ol (178445-89-1) → (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (R)-1-(3-tert-butoxycarbonylmethoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-propyl ester (215169-04-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/S0968-0896(98)00125-4

Reference yield:

3-Hydroxyacetophenone (121-71-1) → (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (R)-1-(3-tert-butoxycarbonylmethoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-propyl ester (215169-04-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / aq. KOH / ethanol / 16 h / 20 °C

2: 76 percent / H₂ / Lindlar catalyst / aq. methanol / 6 h / 2068.59 - 2585.74 Torr

3: 99 percent / K₂CO₃ / acetone / 20 h / 20 °C

4: 98 percent / (+)-DIP-chloride / tetrahydrofuran / -20 °C

5: 72 percent / DMAP; DCC / CH₂Cl₂ / 2 h / 20 °C

With dmap; potassium hydroxide; hydrogen; potassium carbonate; dicyclohexyl-carbodiimide; B-chlorodiisopinocampheylborane; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; 1: Condensation / 2: Hydrogenation / 3: Alkylation / 4: Reduction / 5: Condensation;

DOI:10.1016/S0968-0896(98)00125-4

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-pyrrolidine-2-carboxylic acid (R)-1-(3-tert-butoxycarbonylmethoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-propyl ester (215169-04-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / aq. KOH / ethanol / 16 h / 20 °C

2: 76 percent / H₂ / Lindlar catalyst / aq. methanol / 6 h / 2068.59 - 2585.74 Torr

3: 99 percent / K₂CO₃ / acetone / 20 h / 20 °C

4: 98 percent / (+)-DIP-chloride / tetrahydrofuran / -20 °C

5: 72 percent / DMAP; DCC / CH₂Cl₂ / 2 h / 20 °C

With dmap; potassium hydroxide; hydrogen; potassium carbonate; dicyclohexyl-carbodiimide; B-chlorodiisopinocampheylborane; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; 1: Condensation / 2: Hydrogenation / 3: Alkylation / 4: Reduction / 5: Condensation;

DOI:10.1016/S0968-0896(98)00125-4

upstream raw materials:

(2S)-1-(1,2-dioxo-3 3-dimethylpentyl)-2-pyrrolidinecarboxylic acid

(R)-1-(3-(tert-butoxycarbonylmethoxy)phenyl)-3-(3,4-dimethoxyphenyl)-propan-1-ol

bromoacetic acid tert-butyl ester

3-Hydroxyacetophenone