1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-hydroxypropyl)-N-propylaminopyrrolidine

Base Information

• Chemical Name: 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-hydroxypropyl)-N-propylaminopyrrolidine
• CAS No.: 317861-02-2
• Molecular Formula: C₁₉H₂₈N₂O₇S
• Molecular Weight: 428.507

Synonyms:1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-hydroxypropyl)-N-propylaminopyrrolidine

Chemical Property of 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-hydroxypropyl)-N-propylaminopyrrolidine

Chemical Property:

Purity/Quality:

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Technology Process of 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-hydroxypropyl)-N-propylaminopyrrolidine

There total 8 articles about 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-hydroxypropyl)-N-propylaminopyrrolidine 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: 59.0%

1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxypropyl)-N-propylaminopyrrolidine (317861-01-1) → 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-hydroxypropyl)-N-propylaminopyrrolidine (317861-02-2)

Guidance literature:

With sulfuric acid; hydrogen; 10percent Pd/C; In methanol; for 3h; under 2792.67 Torr;

DOI:10.1021/jm000246e

Reference yield:

4-methoxy-phenyl-sulphonyl chloride (98-68-0) → 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-hydroxypropyl)-N-propylaminopyrrolidine (317861-02-2)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N; DMAP / H₂O; dioxane / 14 h / 20 °C

2: SOCl₂ / 14 h

3: Et₃N / CH₂Cl₂ / 20 °C

4: 79 percent / NaN₃ / dimethylformamide / 26 h / 55 °C

5: 58 percent / H₂; HCOOH / 10percent Pd/C / ethanol; tetrahydrofuran / 16 h / 2792.67 Torr

6: NaCNBH₃; AcONa; AcOH / methanol / 48 °C

7: 44 percent / N-methylmorpholine; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; hydroxybenzotriazole / dimethylformamide / 16 h / 20 °C

8: 59 percent / H₂; H₂SO₄ / 10percent Pd/C / methanol / 3 h / 2792.67 Torr

With 4-methyl-morpholine; dmap; formic acid; thionyl chloride; sodium azide; sulfuric acid; hydrogen; sodium acetate; sodium cyanoborohydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm000246e

Reference yield:

cis-hydroxy-D-proline (2584-71-6,30724-02-8) → 1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-hydroxypropyl)-N-propylaminopyrrolidine (317861-02-2)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N; DMAP / H₂O; dioxane / 14 h / 20 °C

2: SOCl₂ / 14 h

3: Et₃N / CH₂Cl₂ / 20 °C

4: 79 percent / NaN₃ / dimethylformamide / 26 h / 55 °C

5: 58 percent / H₂; HCOOH / 10percent Pd/C / ethanol; tetrahydrofuran / 16 h / 2792.67 Torr

6: NaCNBH₃; AcONa; AcOH / methanol / 48 °C

7: 44 percent / N-methylmorpholine; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; hydroxybenzotriazole / dimethylformamide / 16 h / 20 °C

8: 59 percent / H₂; H₂SO₄ / 10percent Pd/C / methanol / 3 h / 2792.67 Torr

With 4-methyl-morpholine; dmap; formic acid; thionyl chloride; sodium azide; sulfuric acid; hydrogen; sodium acetate; sodium cyanoborohydride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm000246e

upstream raw materials:

1N-(4-methoxybenzenesulfonyl)-2(R)-carbomethoxy-4(S)-N-(1-oxy-2-benzyloxypropyl)-N-propylaminopyrrolidine

4-methoxy-phenyl-sulphonyl chloride

cis-hydroxy-D-proline

(2R,4R)-4-Hydroxy-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylic acid

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