methyl (2S,4R,6R,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate

Base Information

• Chemical Name: methyl (2S,4R,6R,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate
• CAS No.: 516508-65-9
• Molecular Formula: C₂₁H₂₈N₂O₅
• Molecular Weight: 388.464

Synonyms:methyl (2S,4R,6R,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate

Chemical Property of methyl (2S,4R,6R,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate

Chemical Property:

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Technology Process of methyl (2S,4R,6R,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate

There total 2 articles about methyl (2S,4R,6R,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-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: 6.0%

methanol (67-56-1) + di-tert-butyl dicarbonate (24424-99-5) + (S)-6-(2-Amino-2-carboxy-ethyl)-4-phenyl-piperidine-2-carboxylic acid; hydrochloride → methyl (2R,4S,6S,8R)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate + methyl (2R,4S,6S,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate + methyl (2S,4S,6R,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate + methyl (2S,4R,6R,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate (516508-65-9)

Guidance literature:

methanol; (S)-6-(2-Amino-2-carboxy-ethyl)-4-phenyl-piperidine-2-carboxylic acid; hydrochloride; With hydrogenchloride; for 1h;

With triethylamine; In methanol; for 48h; Heating;

di-tert-butyl dicarbonate; With triethylamine; In dichloromethane; for 12h;

DOI:10.1021/jo0355855

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-Amino-3-oxo-7-phenyl-octahydro-indolizine-5-carboxylic acid methyl ester → methyl (2R,4S,6S,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate + methyl (2S,4R,6R,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate (516508-65-9)

Guidance literature:

With triethylamine; In dichloromethane; for 15h;

DOI:10.1021/jo0355855

Reference yield: 82.0%

methyl (2S,4R,6R,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylate (516508-65-9) → (2S,4R,6R,8S)-9-oxo-8-(N-tert-butyloxycarbonylamino)-4-phenyl-1-azabicyclo[4.3.0]nonane-2-carboxylic acid

Guidance literature:

With potassium trimethylsilonate; In diethyl ether; for 2h;

DOI:10.1021/jo0355855

upstream raw materials:

methanol

di-tert-butyl dicarbonate

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