3-Pyrrolidinol, 5-[(4-methoxyphenyl)methyl]-, (3R,5R)-

Base Information

• Chemical Name: 3-Pyrrolidinol, 5-[(4-methoxyphenyl)methyl]-, (3R,5R)-
• CAS No.: 561297-16-3
• Molecular Formula: C12H17NO2
• Molecular Weight: 207.272
• Mol file: 561297-16-3.mol

Synonyms:

Chemical Property of 3-Pyrrolidinol, 5-[(4-methoxyphenyl)methyl]-, (3R,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Pyrrolidinol, 5-[(4-methoxyphenyl)methyl]-, (3R,5R)-

There total 7 articles about 3-Pyrrolidinol, 5-[(4-methoxyphenyl)methyl]-, (3R,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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (3R,5R)-5-(4-Methoxy-benzyl)-pyrrolidin-3-ol (561297-16-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / aq. sodium bicarbonate / tetrahydrofuran / 2 h

2: 93 percent / imidazole / dimethylformamide / 2 h / 20 °C

3: 97 percent / lithium chloride; sodium borohydride / tetrahydrofuran; methanol / 12 h / 20 °C

4: 362 mg / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 0.83 h / -78 °C

5: 445 mg / tetrahydrofuran / 3 h / -78 °C

6: 107 mg / trifluoroacetic acid; triethylsilane / 15 h / 20 °C

With 1H-imidazole; triethylsilane; sodium tetrahydroborate; oxalyl dichloride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4: Swern oxidation;

Reference yield:

(2S,4R)-1-t-butoxycarbonyl-2-{1-hydroxy-1-[4-methoxyphenylmethyl]}-4-[t-butyldimethylsilyloxy]pyrrolidine (561297-15-2) → (3R,5R)-5-(4-Methoxy-benzyl)-pyrrolidin-3-ol (561297-16-3)

Guidance literature:

With triethylsilane; trifluoroacetic acid; at 20 ℃; for 15h;

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → (3R,5R)-5-(4-Methoxy-benzyl)-pyrrolidin-3-ol (561297-16-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / imidazole / dimethylformamide / 2 h / 20 °C

2: 97 percent / lithium chloride; sodium borohydride / tetrahydrofuran; methanol / 12 h / 20 °C

3: 362 mg / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 0.83 h / -78 °C

4: 445 mg / tetrahydrofuran / 3 h / -78 °C

5: 107 mg / trifluoroacetic acid; triethylsilane / 15 h / 20 °C

With 1H-imidazole; triethylsilane; sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3: Swern oxidation;

upstream raw materials:

(2S,4R)-1-t-butoxycarbonyl-2-{1-hydroxy-1-[4-methoxyphenylmethyl]}-4-[t-butyldimethylsilyloxy]pyrrolidine

L-4-hydroxyproline methyl ester hydrochloride

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

(2S,4R)-1-boc-4-tert-butyldimethylsilylpyrrolidine-2-carbaldehyde