methyl (1S,2R,5R)-(+)-9-(benzyloxycarbonyl)-2-ethyl-3-oxo-9-azabicyclo<3.3.1>nonane-2-carboxylate

Base Information

Chemical Name:methyl (1S,2R,5R)-(+)-9-(benzyloxycarbonyl)-2-ethyl-3-oxo-9-azabicyclo<3.3.1>nonane-2-carboxylate
CAS No.:155795-31-6
Molecular Formula:C₂₀H₂₅NO₅
Molecular Weight:359.422
Hs Code.:

Synonyms:methyl (1S,2R,5R)-(+)-9-(benzyloxycarbonyl)-2-ethyl-3-oxo-9-azabicyclo<3.3.1>nonane-2-carboxylate

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Chemical Property of methyl (1S,2R,5R)-(+)-9-(benzyloxycarbonyl)-2-ethyl-3-oxo-9-azabicyclo<3.3.1>nonane-2-carboxylate

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Technology Process of methyl (1S,2R,5R)-(+)-9-(benzyloxycarbonyl)-2-ethyl-3-oxo-9-azabicyclo<3.3.1>nonane-2-carboxylate

There total 4 articles about methyl (1S,2R,5R)-(+)-9-(benzyloxycarbonyl)-2-ethyl-3-oxo-9-azabicyclo<3.3.1>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: 91.0%

: 75-03-6
ethyl iodide

: 155795-30-5
methyl (1S,5R)-(+)-9-(benzyloxycarbonyl)-3-hydroxy-9-azabicyclo<3.3.1>non-2-ene-2-carboxylate

: 155795-31-6
methyl (1S,2R,5R)-(+)-9-(benzyloxycarbonyl)-2-ethyl-3-oxo-9-azabicyclo<3.3.1>nonane-2-carboxylate

Guidance literature:: With sodium hydride; In tetrahydrofuran; methanol; Heating;
DOI:10.1016/S0957-4166(00)86195-9

Reference yield:

: 3-Trimethylsilanyloxy-9-aza-bicyclo[3.3.1]non-2-ene-9-carboxylic acid benzyl ester

: 155795-31-6
methyl (1S,2R,5R)-(+)-9-(benzyloxycarbonyl)-2-ethyl-3-oxo-9-azabicyclo<3.3.1>nonane-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 77 percent / MeLi / hexamethylphosphoric acid triamide; 1,2-dimethoxy-ethane; diethyl ether / 0.5 h / -60 °C

2: 91 percent / NaH / tetrahydrofuran; methanol / 6 h / Heating

With methyllithium; sodium hydride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether;
DOI:10.1039/P19960001567

Reference yield:

: 146747-65-1
(1R,5S)-3-Oxo-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester

: 155795-31-6
methyl (1S,2R,5R)-(+)-9-(benzyloxycarbonyl)-2-ethyl-3-oxo-9-azabicyclo<3.3.1>nonane-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: homochiral lithium amide ⁽⁵⁾ / tetrahydrofuran / -100 °C

2: 1.) MeLi / 1.) HMPA, THF, -60 deg C, 2.) HMPA, THF

3: 91 percent / NaH / tetrahydrofuran; methanol / Heating

With homochiral lithium amide ⁽⁵⁾; methyllithium; sodium hydride; In tetrahydrofuran; methanol;
DOI:10.1016/S0957-4166(00)86195-9