(S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-oxo-8-azabicyclo<3.2.1>octane-6-exo-carboxylate

Base Information

• Chemical Name: (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-oxo-8-azabicyclo<3.2.1>octane-6-exo-carboxylate
• CAS No.: 171779-39-8
• Molecular Formula: C₁₉H₂₃NO₅
• Molecular Weight: 345.395
• Mol file: 171779-39-8.mol

Synonyms:(S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-oxo-8-azabicyclo<3.2.1>octane-6-exo-carboxylate

Chemical Property of (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-oxo-8-azabicyclo<3.2.1>octane-6-exo-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-oxo-8-azabicyclo<3.2.1>octane-6-exo-carboxylate

There total 1 articles about (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-oxo-8-azabicyclo<3.2.1>octane-6-exo-carboxylate 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:

8-Benzyl-2-oxo-8-aza-bicyclo[3.2.1]oct-3-ene-6-carboxylic acid (S)-1-methoxycarbonyl-ethyl ester → (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-oxo-8-azabicyclo<3.2.1>octane-6-exo-carboxylate (171779-39-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 15h; under 735.5 Torr; Yield given; Ambient temperature;

DOI:10.1021/jo00129a053

Reference yield: 61.8%

(S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-oxo-8-azabicyclo<3.2.1>octane-6-exo-carboxylate (171779-39-8) → (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-endo-hydroxy-8-azabicyclo<3.2.1>octane-6-exo-carboxylate + (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-exo-hydroxy-8-azabicyclo<3.2.1>octane-6-exo-carboxylate (171779-40-1)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at -4 ℃; for 3h;

DOI:10.1021/jo00129a053

Reference yield:

(S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-oxo-8-azabicyclo<3.2.1>octane-6-exo-carboxylate (171779-39-8) → 8-Benzyl-2-exo-hydroxy-8-azabicyclo<3.2.1>octane-6-exo-carboxylic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 61.8 percent / LiAl(OtBu)3H / tetrahydrofuran / 3 h / -4 °C

2: 73.5 percent / aq. KOH / methanol / 20 h / Ambient temperature

With potassium hydroxide; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; methanol;

DOI:10.1021/jo00129a053

Downstream raw materials:

(S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-exo-hydroxy-8-azabicyclo<3.2.1>octane-6-exo-carboxylate

(S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-exo-<(tert-butyldimethylsilyl)oxy>-8-azabicyclo<3.2.1>octane-6-exo-carboxylate