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

Base Information

Chemical Name:methyl (1S,5R)-(+)-9-(benzyloxycarbonyl)-3-hydroxy-9-azabicyclo<3.3.1>non-2-ene-2-carboxylate
CAS No.:155795-30-5
Molecular Formula:C₁₈H₂₁NO₅
Molecular Weight:331.368
Hs Code.:

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

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Chemical Property of methyl (1S,5R)-(+)-9-(benzyloxycarbonyl)-3-hydroxy-9-azabicyclo<3.3.1>non-2-ene-2-carboxylate

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Technology Process of methyl (1S,5R)-(+)-9-(benzyloxycarbonyl)-3-hydroxy-9-azabicyclo<3.3.1>non-2-ene-2-carboxylate

There total 3 articles about methyl (1S,5R)-(+)-9-(benzyloxycarbonyl)-3-hydroxy-9-azabicyclo<3.3.1>non-2-ene-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: 77.0%

: 17640-15-2
methyl cyanoformate

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

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

Guidance literature:: With methyllithium; In N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; at -60 ℃; for 0.5h;
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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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

Reference yield:

: 17640-15-2
methyl cyanoformate

: 155795-29-2
(-)-benzyl 3-trimethylsiloxy-9-azabicyclo<3.3.1>non-2-ene-9-carboxylate

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

Guidance literature:: With methyllithium; Yield given. Multistep reaction; 1.) HMPA, THF, -60 deg C, 2.) HMPA, THF;
DOI:10.1016/S0957-4166(00)86195-9