5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione
• CAS No.: 216692-63-6
• Molecular Formula: C₁₈H₂₃N₃O₅S
• Molecular Weight: 393.464
• Mol file: 216692-63-6.mol

Synonyms:5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione

Chemical Property of 5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione

There total 8 articles about 5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione 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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione (216692-63-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / Et₃N, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

2: LiBH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h

3: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

4: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

5: 100 percent / H₂ / Pd/C / ethanol; H₂O; ethyl acetate / 2.5 h

6: Et₃N / dioxane / 10 h / 100 °C

7: aq. HCl / 13.5 h / 90 °C

With 1H-imidazole; hydrogenchloride; dmap; lithium borohydride; sodium azide; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-{2-[1-ethoxy-meth-(E)-ylidene]-butyryl}-urea (216692-41-0) → 5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione (216692-63-6) + 1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-5-ethyl-1H-pyrimidine-2,4-dione

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 90 ℃; for 13.5h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine (118329-82-1) → 5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione (216692-63-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

2: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

3: 100 percent / H₂ / Pd/C / ethanol; H₂O; ethyl acetate / 2.5 h

4: Et₃N / dioxane / 10 h / 100 °C

5: aq. HCl / 13.5 h / 90 °C

With 1H-imidazole; hydrogenchloride; dmap; sodium azide; hydrogen; triethylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00821-7

upstream raw materials:

1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-{2-[1-ethoxy-meth-(E)-ylidene]-butyryl}-urea

(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

L-4-hydroxyproline methyl ester hydrochloride

N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester

Downstream raw materials:

Acetic acid (2S,4S)-4-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester