[(1R,2R)-2-acetoxy-1-{(R)-[acetyl(methyl)amino](phenyl)methyl}cyclopentyl]methyl acetate

Base Information

• Chemical Name: [(1R,2R)-2-acetoxy-1-{(R)-[acetyl(methyl)amino](phenyl)methyl}cyclopentyl]methyl acetate
• CAS No.: 607405-17-4
• Molecular Formula: C₂₀H₂₇NO₅
• Molecular Weight: 361.438
• Mol file: 607405-17-4.mol

Synonyms:[(1R,2R)-2-acetoxy-1-{(R)-[acetyl(methyl)amino](phenyl)methyl}cyclopentyl]methyl acetate

Chemical Property of [(1R,2R)-2-acetoxy-1-{(R)-[acetyl(methyl)amino](phenyl)methyl}cyclopentyl]methyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2R)-2-acetoxy-1-{(R)-[acetyl(methyl)amino](phenyl)methyl}cyclopentyl]methyl acetate

There total 7 articles about [(1R,2R)-2-acetoxy-1-{(R)-[acetyl(methyl)amino](phenyl)methyl}cyclopentyl]methyl acetate 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:

tert-butyl 2-oxocyclopentanecarboxylate (84109-76-2) + acetic anhydride (108-24-7) + benzaldehyde N-boc imine (150884-50-7) → Acetic acid (1S,2S)-2-acetoxymethyl-2-[(S)-(acetyl-methyl-amino)-phenyl-methyl]-cyclopentyl ester + [(1R,2R)-2-acetoxy-1-{(R)-[acetyl(methyl)amino](phenyl)methyl}cyclopentyl]methyl acetate (607405-17-4)

Guidance literature:

tert-butyl 2-oxocyclopentanecarboxylate; benzaldehyde N-boc imine; In tetrahydrofuran; at 0 ℃; for 5h;

With lithium aluminium tetrahydride; In tetrahydrofuran; for 24h; Heating;

acetic anhydride; With pyridine; for 12h; Title compound not separated from byproducts;

DOI:10.1002/anie.200462202

Reference yield:

methyl 2-oxocyclopentane-1-carboxylate (10472-24-9,265317-94-0) + acetyl chloride (75-36-5) + benzylidine-carbamic acid allyl ester (865086-22-2) → Acetic acid (1S,2S)-2-acetoxymethyl-2-[(S)-(acetyl-methyl-amino)-phenyl-methyl]-cyclopentyl ester + [(1R,2R)-2-acetoxy-1-{(R)-[acetyl(methyl)amino](phenyl)methyl}cyclopentyl]methyl acetate (607405-17-4)

Guidance literature:

methyl 2-oxocyclopentane-1-carboxylate; benzylidine-carbamic acid allyl ester; With Cinchonin; In dichloromethane; at -55 ℃; for 2h;

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 24h;

acetyl chloride; With pyridine; at 20 ℃; for 12h; Title compound not separated from byproducts;

DOI:10.1021/ol060304b

Reference yield:

C-phenyl-N-methylnitrone (3376-23-6,7372-59-0,59862-60-1) → [(1R,2R)-2-acetoxy-1-{(R)-[acetyl(methyl)amino](phenyl)methyl}cyclopentyl]methyl acetate (607405-17-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: chiral pyrrolidine derivative dihydrochloride / dimethylformamide; H₂O / 72 h / 10 °C

1.2: NaBH₄ / methanol / 0.5 h / 20 °C

2.1: hydrogen; aq. HCl / Pd(OH)2/C / methanol / 20 °C

3.1: pyridine / CH₂Cl₂ / 1 h

With pyridine; hydrogenchloride; chiral pyrrolidine derivative dihydrochloride; hydrogen; palladium dihydroxide; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200300172

upstream raw materials:

acetyl chloride

tert-butyl 2-oxocyclopentanecarboxylate

acetic anhydride

benzaldehyde N-boc imine