methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate

Base Information

• Chemical Name: methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate
• CAS No.: 1383973-51-0
• Molecular Formula: C₁₈H₂₃NO₄
• Molecular Weight: 317.385
• Mol file: 1383973-51-0.mol

Synonyms:methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate

Chemical Property of methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate

There total 5 articles about methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-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: 99.0%

bicyclo[3.2.1]octane-1,5-dicarboxylic acid monomethyl ester (110371-27-2) + benzyl alcohol (100-51-6,185532-71-2) → methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate (1383973-51-0)

Guidance literature:

bicyclo[3.2.1]octane-1,5-dicarboxylic acid monomethyl ester; With diphenyl phosphoryl azide; triethylamine; In toluene; at 18 - 25 ℃; for 4h; Inert atmosphere; Reflux;

benzyl alcohol; In toluene; Reflux;

Reference yield:

cyclohexane-1,3-dicarboxylic acid (3971-31-1) → methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate (1383973-51-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: chloro-trimethyl-silane / 96 h / 18 - 25 °C / Inert atmosphere

2.1: diisopropylamine; n-butyllithium / hexane; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 25 °C

3.1: diisopropylamine; n-butyllithium / hexane; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrahydrofuran / -78 - 25 °C / Inert atmosphere

4.1: water; barium hydroxide octahydrate / ethanol / Inert atmosphere; Reflux

4.2: 18 - 25 °C / pH 1 - 2

5.1: triethylamine; diphenyl phosphoryl azide / toluene / 4 h / 18 - 25 °C / Inert atmosphere; Reflux

5.2: Reflux

With n-butyllithium; chloro-trimethyl-silane; barium hydroxide octahydrate; diphenyl phosphoryl azide; water; triethylamine; diisopropylamine; In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ethanol; hexane; toluene; 5.1: Curtius Rearrangement;

Reference yield:

dimethyl 1-(2'-chloroethyl)cyclohexane-1,3-dicarboxylate (106004-10-8) → methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate (1383973-51-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisopropylamine; n-butyllithium / hexane; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrahydrofuran / -78 - 25 °C / Inert atmosphere

2.1: water; barium hydroxide octahydrate / ethanol / Inert atmosphere; Reflux

2.2: 18 - 25 °C / pH 1 - 2

3.1: triethylamine; diphenyl phosphoryl azide / toluene / 4 h / 18 - 25 °C / Inert atmosphere; Reflux

3.2: Reflux

With n-butyllithium; barium hydroxide octahydrate; diphenyl phosphoryl azide; water; triethylamine; diisopropylamine; In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; ethanol; hexane; toluene; 3.1: Curtius Rearrangement;

upstream raw materials:

dimethyl cyclohexane-1,3-dicarboxylate

bicyclo[3.2.1]octane-1,5-dicarboxylic acid monomethyl ester

benzyl alcohol

cyclohexane-1,3-dicarboxylic acid

Downstream raw materials:

benzyl 5-aminobicyclo[3.2.1]octan-1-ylcarbamate

N-(5-aminobicyclo[3.2.1]octan-1-yl)-3-fluorobenzamide

methyl 5-aminobicyclo[3.2.1]octane-1-carboxylate

benzyl 5-carbamoylbicyclo[3.2.1]octan-1-ylcarbamate