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

Base Information

• Chemical Name: (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-exo-<(tert-butyldimethylsilyl)oxy>-8-azabicyclo<3.2.1>octane-6-exo-carboxylate
• CAS No.: 171779-43-4
• Molecular Formula: C₂₅H₃₉NO₅Si
• Molecular Weight: 461.674
• Mol file: 171779-43-4.mol

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

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

There total 3 articles about (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-exo-<(tert-butyldimethylsilyl)oxy>-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: 96.0%

t-butyldimethylsiyl triflate (69739-34-0) + (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-exo-hydroxy-8-azabicyclo<3.2.1>octane-6-exo-carboxylate (171779-40-1) → (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-exo-<(tert-butyldimethylsilyl)oxy>-8-azabicyclo<3.2.1>octane-6-exo-carboxylate (171779-43-4)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1021/jo00129a053

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-exo-<(tert-butyldimethylsilyl)oxy>-8-azabicyclo<3.2.1>octane-6-exo-carboxylate (171779-43-4)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 5percent Pd/C / ethyl acetate / 15 h / 735.5 Torr / Ambient temperature

2: 61.8 percent / LiAl(OtBu)3H / tetrahydrofuran / 3 h / -4 °C

3: 96 percent / NEt₃ / CH₂Cl₂

With hydrogen; lithium tri-t-butoxyaluminum hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;

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) → (S)-1-(Methoxycarbonyl)etyl 8-benzyl-2-exo-<(tert-butyldimethylsilyl)oxy>-8-azabicyclo<3.2.1>octane-6-exo-carboxylate (171779-43-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 96 percent / NEt₃ / CH₂Cl₂

With lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00129a053

upstream raw materials:

t-butyldimethylsiyl triflate

(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-oxo-8-azabicyclo<3.2.1>octane-6-exo-carboxylate