ENDO-1-AZABICYCLO[2.2.1]HEPTANE-3-CARBOXYLIC ACID, ETHYL ESTER

Base Information

• Chemical Name: ENDO-1-AZABICYCLO[2.2.1]HEPTANE-3-CARBOXYLIC ACID, ETHYL ESTER
• CAS No.: 133366-43-5
• Molecular Formula: C₉H₁₅NO₂
• Molecular Weight: 169.224
• Mol file: 133366-43-5.mol

Synonyms:ENDO-1-AZABICYCLO[2.2.1]HEPTANE-3-CARBOXYLIC ACID, ETHYL ESTER

Chemical Property of ENDO-1-AZABICYCLO[2.2.1]HEPTANE-3-CARBOXYLIC ACID, ETHYL ESTER

Chemical Property:

• PSA: 29.54000
• LogP: 0.43910

Purity/Quality:

98%min ^*data from raw suppliers

ENDO-1-AZABICYCLO-[2.2.1]-HEPTANE-3-CARBOXYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ENDO-1-AZABICYCLO[2.2.1]HEPTANE-3-CARBOXYLIC ACID, ETHYL ESTER

There total 13 articles about ENDO-1-AZABICYCLO[2.2.1]HEPTANE-3-CARBOXYLIC ACID, ETHYL 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: 70.0%

(1R,3S,4S)-1-Benzyl-3-ethoxycarbonyl-1-azonia-bicyclo[2.2.1]heptane; bromide (133745-58-1) → (1R,3R,4R)-1-Aza-bicyclo[2.2.1]heptane-3-carboxylic acid ethyl ester (114704-10-8,115594-72-4,133366-43-5,133444-97-0,133813-64-6,133813-65-7,134234-17-6,137940-37-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4039(00)92055-0

Reference yield:

cinchomeronic anhydride (4664-08-8) → (1R,3R,4R)-1-Aza-bicyclo[2.2.1]heptane-3-carboxylic acid ethyl ester (114704-10-8,115594-72-4,133366-43-5,133444-97-0,133813-64-6,133813-65-7,134234-17-6,137940-37-5)

Guidance literature:

Multi-step reaction with 7 steps

1: NaBH₄ / toluene; dimethylformamide / 1.5 h / -20 - 35 °C

2: 5 M HCl / 0.5 h / Heating

3: H₂, AcOH / 10percent Rh/C / ethanol / 24 h / 90 °C / 51714.8 Torr

4: K₂CO₃ / ethanol / 0.75 h / Ambient temperature

5: HBr (gas) / 216 h / Ambient temperature

6: aq. K₂CO₃

7: H₂, AcOH / 10percent Pd/C / ethanol / 40 °C / 760 Torr

With hydrogenchloride; sodium tetrahydroborate; hydrogen bromide; hydrogen; potassium carbonate; acetic acid; palladium on activated charcoal; Rh on carbon; In ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00113a009

Reference yield:

5,6-dihydro-pyran-2-one (3393-45-1) → endo-ethyl 1-azabicyclo[2.2.1]heptane-3-carboxylate (114704-10-8,115594-72-4,133366-43-5,133444-97-0,133813-64-6,133813-65-7,134234-17-6,137940-37-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) HBr gas, 2.) aq. K₂CO₃, 3.) H₂ / 3.) 10percent Pd/C

With hydrogen bromide; hydrogen; potassium carbonate; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane;

DOI:10.1021/jm00091a007

upstream raw materials:

cis-2-benzylhexahydropyrano<3,4-c>pyrrol-4(3aH)-one

(1R,3R,4S)-1-Benzyl-3-ethoxycarbonyl-1-azonia-bicyclo[2.2.1]heptane; bromide

(1R,3S,4S)-1-Benzyl-3-ethoxycarbonyl-1-azonia-bicyclo[2.2.1]heptane; bromide

5,6-dihydro-pyran-2-one

Downstream raw materials:

(1R,3S,4R)-1-Aza-bicyclo[2.2.1]heptane-3-carboxylic acid

(1R,3S,4R)-1-Aza-bicyclo[2.2.1]heptane-3-carbonyl chloride

endo-3-acetyl-1-azabicyclo<2.2.1>heptane

exo-methyl 1-azabicyclo<2.2.1>heptane-3-carboxylate