(3R,6S,9S)-1-aza-2-oxo-3-benzylamino-3-allyl-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane

Base Information

• Chemical Name: (3R,6S,9S)-1-aza-2-oxo-3-benzylamino-3-allyl-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane
• CAS No.: 758719-32-3
• Molecular Formula: C₂₃H₃₂N₂O₃
• Molecular Weight: 384.519
• Mol file: 758719-32-3.mol

Synonyms:(3R,6S,9S)-1-aza-2-oxo-3-benzylamino-3-allyl-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane

Chemical Property of (3R,6S,9S)-1-aza-2-oxo-3-benzylamino-3-allyl-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,6S,9S)-1-aza-2-oxo-3-benzylamino-3-allyl-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane

There total 6 articles about (3R,6S,9S)-1-aza-2-oxo-3-benzylamino-3-allyl-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane 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:

(3S,6R,8aR)-6-Benzyloxycarbonylamino-5-oxo-octahydro-indolizine-3-carboxylic acid tert-butyl ester → (3R,6S,9S)-1-aza-2-oxo-3-benzylamino-3-allyl-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane (758719-32-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: H₂ / Pd/C / methanol

2.1: Et₃N; MgSO₄ / CH₂Cl₂ / 24 h / 20 °C

3.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

3.2: tetrahydrofuran / 20 °C

4.1: NaBH₄ / methanol / 0.25 h

With sodium tetrahydroborate; hydrogen; magnesium sulfate; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1055/s-2006-926370

Reference yield:

C20H26N2O5 + benzaldehyde (100-52-7) + allyl bromide (106-95-6) → (3S,6S,9S)-1-aza-2-oxo-3-benzylamino-3-allyl-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane + (3R,6S,9S)-1-aza-2-oxo-3-benzylamino-3-allyl-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane (758719-32-3)

Guidance literature:

C₂₀H₂₆N₂O₅; With hydrogen; palladium 10% on activated carbon; In methanol; at -50 ℃;

benzaldehyde; With magnesium sulfate; triethylamine; In dichloromethane; at -50 ℃;

allyl bromide; With sodium tetrahydroborate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; at -50 ℃;

Reference yield:

allyl bromide (106-95-6) + 1-aza-2-oxo-3-benzylidenamino-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane → (3S,6S,9S)-1-aza-2-oxo-3-benzylamino-3-allyl-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane + (3R,6S,9S)-1-aza-2-oxo-3-benzylamino-3-allyl-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane (758719-32-3)

Guidance literature:

1-aza-2-oxo-3-benzylidenamino-9-(tert-butoxycarbonyl)bicyclo[4.3.0]nonane; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.333333h;

allyl bromide; In tetrahydrofuran; at -50 ℃; for 5h;

With sodium tetrahydroborate; In methanol; Further stages.;

DOI:10.1016/j.tetlet.2004.06.077

upstream raw materials:

allyl bromide

benzaldehyde