(3R,5R)-5-[2-[2-[2-(3-METHOXYPHENYL)ETHYL]PHENOXY]ETHYL]-1-METHYL-3-PYRROLIDINOL HYDROCHLORIDE

Base Information

• Chemical Name: (3R,5R)-5-[2-[2-[2-(3-METHOXYPHENYL)ETHYL]PHENOXY]ETHYL]-1-METHYL-3-PYRROLIDINOL HYDROCHLORIDE
• CAS No.: 167144-79-8
• Molecular Formula: C22H29 N O3
• Molecular Weight: 355.477
• Mol file: 167144-79-8.mol

Synonyms:3-Pyrrolidinol,5-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-1-methyl-, (3R-trans)-

Chemical Property of (3R,5R)-5-[2-[2-[2-(3-METHOXYPHENYL)ETHYL]PHENOXY]ETHYL]-1-METHYL-3-PYRROLIDINOL HYDROCHLORIDE

Chemical Property:

• Vapor Pressure: 3.35E-10mmHg at 25°C
• Boiling Point: 484.5°Cat760mmHg
• Flash Point: 246.8°C
• PSA: 41.93000
• Density: g/cm³
• LogP: 4.05420
• Storage Temp.: Store at RT

Purity/Quality:

98%Min ^*data from raw suppliers

R-96544 hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: R-96544 Hydrochloride is a the active form of a novel 5-HT2A receptor antagonist R-102444. It inhibits the platelet aggregation induced by serotonin (5-hydroxytryptamine, 5-HT).

Technology Process of (3R,5R)-5-[2-[2-[2-(3-METHOXYPHENYL)ETHYL]PHENOXY]ETHYL]-1-METHYL-3-PYRROLIDINOL HYDROCHLORIDE

There total 5 articles about (3R,5R)-5-[2-[2-[2-(3-METHOXYPHENYL)ETHYL]PHENOXY]ETHYL]-1-METHYL-3-PYRROLIDINOL HYDROCHLORIDE 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: 95.0%

(2R,4R)-1-ethoxycarbonyl-4-hydroxy-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]pyrrolidine (167145-84-8) → (2R,4R)-4-hydroxy-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-1-methylpyrrolidine (167144-79-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1248/cpb.48.1729

Reference yield:

(2R,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(2-hydroxyethyl)pyrrolidine (318511-16-9) → (2R,4R)-4-hydroxy-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-1-methylpyrrolidine (167144-79-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / Et₃N / CH₂Cl₂ / 2.5 h / 20 °C

2.1: t-BuOK / N,N-dimethyl-acetamide / 0.17 h / 0 °C

2.2: 80 percent / N,N-dimethyl-acetamide / 4 h / 20 °C

3.1: 93 percent / H₂ / 5 percent Pd/C / ethanol / 7 h / 60 °C

4.1: 95 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

With lithium aluminium tetrahydride; potassium tert-butylate; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide;

DOI:10.1248/cpb.48.1729

Reference yield:

(2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(ethoxycarbonylmethyl)pyrrolidine (318511-15-8) → (2R,4R)-4-hydroxy-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-1-methylpyrrolidine (167144-79-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 85 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / -10 °C

2.1: 80 percent / Et₃N / CH₂Cl₂ / 2.5 h / 20 °C

3.1: t-BuOK / N,N-dimethyl-acetamide / 0.17 h / 0 °C

3.2: 80 percent / N,N-dimethyl-acetamide / 4 h / 20 °C

4.1: 93 percent / H₂ / 5 percent Pd/C / ethanol / 7 h / 60 °C

5.1: 95 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

With lithium aluminium tetrahydride; potassium tert-butylate; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide;

DOI:10.1248/cpb.48.1729

upstream raw materials:

(2R,4R)-1-ethoxycarbonyl-4-hydroxy-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]pyrrolidine

(2R,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(2-hydroxyethyl)pyrrolidine

(2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(ethoxycarbonylmethyl)pyrrolidine

(2R,4R)-4-benzyloxy-1-ethoxycarbonyl-2-[2-(p-toluenesulfonyloxy)ethyl]pyrrolidine

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