1-Pyrrolidinecarboxylic acid, 3-hydroxy-2-(hydroxymethyl)-5-(1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-5- pyrimidinyl)-, phenylmethyl ester, (2R,5R)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 3-hydroxy-2-(hydroxymethyl)-5-(1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-5- pyrimidinyl)-, phenylmethyl ester, (2R,5R)-
• CAS No.: 646521-60-0
• Molecular Formula: C18H21N3O6
• Molecular Weight: 375.381
• Mol file: 646521-60-0.mol

Synonyms:

Chemical Property of 1-Pyrrolidinecarboxylic acid, 3-hydroxy-2-(hydroxymethyl)-5-(1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-5- pyrimidinyl)-, phenylmethyl ester, (2R,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Pyrrolidinecarboxylic acid, 3-hydroxy-2-(hydroxymethyl)-5-(1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-5- pyrimidinyl)-, phenylmethyl ester, (2R,5R)-

There total 2 articles about 1-Pyrrolidinecarboxylic acid, 3-hydroxy-2-(hydroxymethyl)-5-(1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-5- pyrimidinyl)-, phenylmethyl ester, (2R,5R)- 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: 77.0%

methyl iodide (74-88-4) + (2R,5R)-5-(2,4-Dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester (646521-59-7) → (2R,5R)-3-Hydroxy-2-hydroxymethyl-5-(1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester (646521-60-0)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; In dichloromethane; at 20 ℃; for 70h;

DOI:10.1081/NCN-120022832

Reference yield:

N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-4-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-3-cyclopenten (325771-77-5) → (2R,5R)-3-Hydroxy-2-hydroxymethyl-5-(1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester (646521-60-0)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 37 h / -15 - 20 °C

2: NaB(OAc)3H; acetic acid / acetonitrile / 0.33 h / -15 - 20 °C

3: 77 percent / N,O-bis(trimethylsilyl) acetamide / CH₂Cl₂ / 70 h / 20 °C

With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1081/NCN-120022832

Reference yield:

(2R,5R)-3-Hydroxy-2-hydroxymethyl-5-(1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester (646521-60-0) → N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-(dimethoxytrityl-hydroxymethyl)-pyrrolidine (325771-86-6)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen / Pd/C / methanol / 20 °C

2: NaHCO₃ / tetrahydrofuran; dioxane / 3 h / 20 °C

3: 65 percent / pyridine / 2 h / 20 °C

With pyridine; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1081/NCN-120022832

upstream raw materials:

methyl iodide

(2R,5R)-5-(2,4-Dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-4-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-3-cyclopenten

Downstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-(dimethoxytrityl-hydroxymethyl)-pyrrolidine