3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.1]heptane-1-carboxylic acid

Base Information

• Chemical Name: 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.1]heptane-1-carboxylic acid
• CAS No.: 1000931-22-5
• Molecular Formula: C₁₂H₁₉NO₄
• Molecular Weight: 241.287
• Mol file: 1000931-22-5.mol

Synonyms:

Chemical Property of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.1]heptane-1-carboxylic acid

Chemical Property:

• Boiling Point: 363.3±25.0 °C(Predicted)
• PKA: 4.53±0.20(Predicted)
• Density: 1.266±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

97% ^*data from raw suppliers

3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.1]heptane-1-carboxylicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.1]heptane-1-carboxylic acid

There total 14 articles about 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.1]heptane-1-carboxylic acid 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:

C12H19NO3 (1640998-93-1) → 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.1]heptane-1-carboxylic acid (1000931-22-5)

Guidance literature:

With sodium chlorite; disodium hydrogenphosphate; In tetrahydrofuran; water; tert-butyl alcohol; at 20 ℃; for 1h;

DOI:10.1055/s-0033-1340322

Reference yield:

3,3-dimethoxycyclobutane-1,1-dicarboxylic acid diisopropyl ester (115118-68-8) → 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.1]heptane-1-carboxylic acid (1000931-22-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: hydrogenchloride / water

2.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 15 °C

2.2: 20 °C

3.1: 5%-palladium/activated carbon; hydrogen / methanol / 50 °C / 37503.8 Torr

4.1: hydrazine hydrate / ethanol / 48 h / Reflux

5.1: hydrogenchloride; sodium nitrite / water; diethyl ether / 0.25 h / 0 °C

6.1: toluene / 2 h / 105 - 110 °C

6.2: 24 h / Reflux

7.1: hydrogenchloride / ethyl acetate / 20 °C

8.1: sodium methylate / methanol / 60 h / Reflux

8.2: κ?-2 resin / 0.5 h

9.1: dimethylsulfide borane complex / tetrahydrofuran / 36 h / Reflux

9.2: 0.5 h

10.1: dichloromethane / 1.5 h / 20 °C

11.1: Dess-Martin periodane / dichloromethane / 15 h / 20 °C / Reflux

12.1: sodium chlorite; disodium hydrogenphosphate / water; tetrahydrofuran; tert-butyl alcohol / 1 h / 20 °C

With hydrogenchloride; sodium chlorite; disodium hydrogenphosphate; dimethylsulfide borane complex; 5%-palladium/activated carbon; hydrogen; sodium methylate; sodium hydride; Dess-Martin periodane; hydrazine hydrate; sodium nitrite; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; toluene; mineral oil; tert-butyl alcohol; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination / 6.1: |Curtius Rearrangement / 6.2: |Curtius Rearrangement;

DOI:10.1055/s-0033-1340322

Reference yield:

dipropan-2-yl 3-oxocyclobutane-1,1-dicarboxylate (893724-10-2) → 3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.1]heptane-1-carboxylic acid (1000931-22-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 15 °C

1.2: 20 °C

2.1: 5%-palladium/activated carbon; hydrogen / methanol / 50 °C / 37503.8 Torr

3.1: hydrazine hydrate / ethanol / 48 h / Reflux

4.1: hydrogenchloride; sodium nitrite / water; diethyl ether / 0.25 h / 0 °C

5.1: toluene / 2 h / 105 - 110 °C

5.2: 24 h / Reflux

6.1: hydrogenchloride / ethyl acetate / 20 °C

7.1: sodium methylate / methanol / 60 h / Reflux

7.2: κ?-2 resin / 0.5 h

8.1: dimethylsulfide borane complex / tetrahydrofuran / 36 h / Reflux

8.2: 0.5 h

9.1: dichloromethane / 1.5 h / 20 °C

10.1: Dess-Martin periodane / dichloromethane / 15 h / 20 °C / Reflux

11.1: sodium chlorite; disodium hydrogenphosphate / water; tetrahydrofuran; tert-butyl alcohol / 1 h / 20 °C

With hydrogenchloride; sodium chlorite; disodium hydrogenphosphate; dimethylsulfide borane complex; 5%-palladium/activated carbon; hydrogen; sodium methylate; sodium hydride; Dess-Martin periodane; hydrazine hydrate; sodium nitrite; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; toluene; mineral oil; tert-butyl alcohol; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination / 5.1: |Curtius Rearrangement / 5.2: |Curtius Rearrangement;

DOI:10.1055/s-0033-1340322

upstream raw materials:

3,3-dimethoxycyclobutane-1,1-dicarboxylic acid diisopropyl ester

dipropan-2-yl 3-oxocyclobutane-1,1-dicarboxylate

diisopropyl 3-((methoxycarbonyl)methylidene)cyclobutane-1,1-dicarboxylate

diisopropyl 3-((methoxycarbonyl)methyl)cyclobutane-1,1-dicarboxylate