benzyl 4-hydroxybicyclo[2.2.1]heptan-1-ylcarbamate

Base Information

• Chemical Name: benzyl 4-hydroxybicyclo[2.2.1]heptan-1-ylcarbamate
• CAS No.: 1403865-38-2
• Molecular Formula: C₁₅H₁₉NO₃
• Molecular Weight: 261.321
• Mol file: 1403865-38-2.mol

Synonyms:benzyl 4-hydroxybicyclo[2.2.1]heptan-1-ylcarbamate

Chemical Property of benzyl 4-hydroxybicyclo[2.2.1]heptan-1-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4-hydroxybicyclo[2.2.1]heptan-1-ylcarbamate

There total 8 articles about benzyl 4-hydroxybicyclo[2.2.1]heptan-1-ylcarbamate 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: 69.0%

4-Hydroxybicyclo<2.2.1>heptane-1-carboxylic Acid (88888-30-6) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 4-hydroxybicyclo[2.2.1]heptan-1-ylcarbamate (1403865-38-2)

Guidance literature:

With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine; In toluene; at 10 - 110 ℃; for 20h; Inert atmosphere;

Reference yield:

cyclopentane-1,3-dicarboxylic acid (4056-78-4,826-02-8) → benzyl 4-hydroxybicyclo[2.2.1]heptan-1-ylcarbamate (1403865-38-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sulfuric acid / 16 h / 7 - 12 °C / Reflux

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine / tetrahydrofuran; hexanes / 2 h / -73 - -10 °C / Inert atmosphere

2.2: 16 h / -70 - 20 °C

3.1: water; sodium hydroxide / tetrahydrofuran; methanol / 16 h / 15 - 20 °C

3.2: 10 °C / pH ~ 4

4.1: diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine / toluene / 2 h / 10 - 110 °C

4.2: 40 h / 110 °C

5.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 10 h / 1551.49 Torr

6.1: acetic acid; sodium nitrite / water / 65 °C

6.2: 5 h / 65 °C

6.3: pH 3

7.1: diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine / toluene / 20 h / 10 - 110 °C / Inert atmosphere

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sulfuric acid; diphenyl phosphoryl azide; water; hydrogen; acetic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; sodium nitrite; palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexanes; water; toluene;

Reference yield:

norborn-2-ene (498-66-8) → benzyl 4-hydroxybicyclo[2.2.1]heptan-1-ylcarbamate (1403865-38-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: ruthenium trichloride; sodium periodate / water; ethyl acetate; acetonitrile / 5 - 39 °C / Industry scale

2.1: sulfuric acid / 16 h / 7 - 12 °C / Reflux

3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine / tetrahydrofuran; hexanes / 2 h / -73 - -10 °C / Inert atmosphere

3.2: 16 h / -70 - 20 °C

4.1: water; sodium hydroxide / tetrahydrofuran; methanol / 16 h / 15 - 20 °C

4.2: 10 °C / pH ~ 4

5.1: diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine / toluene / 2 h / 10 - 110 °C

5.2: 40 h / 110 °C

6.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / methanol / 10 h / 1551.49 Torr

7.1: acetic acid; sodium nitrite / water / 65 °C

7.2: 5 h / 65 °C

7.3: pH 3

8.1: diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine / toluene / 20 h / 10 - 110 °C / Inert atmosphere

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; ruthenium trichloride; sodium periodate; n-butyllithium; sulfuric acid; diphenyl phosphoryl azide; water; hydrogen; acetic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; sodium nitrite; palladium 10% on activated carbon; In tetrahydrofuran; methanol; hexanes; water; ethyl acetate; toluene; acetonitrile;

upstream raw materials:

cyclopentane-1,3-dicarboxylic acid

norborn-2-ene

4-Hydroxybicyclo<2.2.1>heptane-1-carboxylic Acid

benzyl alcohol