(1S,3S,5R)-3-formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (1S,3S,5R)-3-formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester
• CAS No.: 882036-78-4
• Molecular Formula: C₁₃H₂₁NO₃
• Molecular Weight: 239.315

Synonyms:(1S,3S,5R)-3-formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Chemical Property of (1S,3S,5R)-3-formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

99%, ^*data from raw suppliers

exo-tert-Butyl3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate 97% ^*data from reagent suppliers

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Technology Process of (1S,3S,5R)-3-formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

There total 4 articles about (1S,3S,5R)-3-formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 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:

tert-butyl 3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate (799283-62-8) → (1S,3R,5R)-3-Formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (882041-98-7) + (1S,3S,5R)-3-formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (882036-78-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -70 ℃; for 0.166667 - 0.25h;

With triethylamine; In dichloromethane; at -70 ℃; for 0.5h;

tert-butyl 3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate; In dichloromethane; at -70 - 20 ℃; for 1.25h;

Reference yield:

(+/-)-(1S,5R)-3-[1-methoxy-meth-(Z)-ylidene]-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester → (1S,3R,5R)-3-Formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (882041-98-7) + (1S,3S,5R)-3-formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (882036-78-4)

Guidance literature:

With trichloroacetic acid; In dichloromethane; water; at 20 ℃;

Reference yield:

tert-butyl 3-methylidene-8-azabicyclo[3.2.1]octane-8-carboxylate → (1S,3R,5R)-3-Formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (882041-98-7) + (1S,3S,5R)-3-formyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (882036-78-4)

Guidance literature:

Multi-step reaction with 2 steps

1: selenium(IV) oxide; tert.-butylhydroperoxide / dichloromethane; decane / 4 h / 0 °C

2: [Ir(2-(2,4-difluorophenyl)-4-(trifluoromethyl)pyridine)₂(5,5'-bis(trifluoromethyl)-2,2'-bipyridine)]PF₆; 2,4,6-trimethyl-pyridine; tetrabutylphosphonium 2,2,2-trifluoroacetate / 24 h / 35 °C / Irradiation; Sealed tube; Inert atmosphere

With 2,4,6-trimethyl-pyridine; tert.-butylhydroperoxide; selenium(IV) oxide; tetrabutylphosphonium 2,2,2-trifluoroacetate; [Ir(2-(2,4-difluorophenyl)-4-(trifluoromethyl)pyridine)₂(5,5'-bis(trifluoromethyl)-2,2'-bipyridine)]PF₆; In decane; dichloromethane;

DOI:10.1002/anie.202105285

upstream raw materials:

tert-butyl 3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

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