methyl-[4-(3-oxo-propyl)-cyclohexyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: methyl-[4-(3-oxo-propyl)-cyclohexyl]-carbamic acid tert-butyl ester
• CAS No.: 400899-12-9
• Molecular Formula: C₁₅H₂₇NO₃
• Molecular Weight: 269.384
• Mol file: 400899-12-9.mol

Synonyms:methyl-[4-(3-oxo-propyl)-cyclohexyl]-carbamic acid tert-butyl ester

Chemical Property of methyl-[4-(3-oxo-propyl)-cyclohexyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-[4-(3-oxo-propyl)-cyclohexyl]-carbamic acid tert-butyl ester

There total 8 articles about methyl-[4-(3-oxo-propyl)-cyclohexyl]-carbamic 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:

[4-(3-hydroxy-propyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester (400899-11-8) → methyl-[4-(3-oxo-propyl)-cyclohexyl]-carbamic acid tert-butyl ester (400899-12-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.2533/000942905777676858

Reference yield:

trans-(4-formylcyclohexyl)methylcarbamic acid tert-butyl ester (400898-94-4) → methyl-[4-(3-oxo-propyl)-cyclohexyl]-carbamic acid tert-butyl ester (400899-12-9)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOMe / ethanol / 20 °C

2: H₂ / Pd/C / methanol / 20 °C

3: LiBH₄ / tetrahydrofuran / Heating

4: DMSO; oxalyl chloride; NEt₃ / CH₂Cl₂ / -78 - 20 °C

With lithium borohydride; oxalyl dichloride; hydrogen; sodium methylate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1: Horner-Wadsworth-Emmons reaction / 4: Swern oxidation;

DOI:10.2533/000942905777676858

Reference yield:

tert-butyl ((1r,4r)-4-(hydroxymethyl)cyclohexyl)(methyl)carbamate (400899-08-3) → methyl-[4-(3-oxo-propyl)-cyclohexyl]-carbamic acid tert-butyl ester (400899-12-9)

Guidance literature:

Multi-step reaction with 5 steps

1: DMSO; oxalyl chloride; NEt₃ / CH₂Cl₂ / -78 - 20 °C

2: NaOMe / ethanol / 20 °C

3: H₂ / Pd/C / methanol / 20 °C

4: LiBH₄ / tetrahydrofuran / Heating

5: DMSO; oxalyl chloride; NEt₃ / CH₂Cl₂ / -78 - 20 °C

With lithium borohydride; oxalyl dichloride; hydrogen; sodium methylate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1: Swern oxidation / 2: Horner-Wadsworth-Emmons reaction / 5: Swern oxidation;

DOI:10.2533/000942905777676858

upstream raw materials:

[4-(3-hydroxy-propyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester

trans-(4-formylcyclohexyl)methylcarbamic acid tert-butyl ester

tert-butyl ((1r,4r)-4-(hydroxymethyl)cyclohexyl)(methyl)carbamate

methyl (1R,4R)-4-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate

Downstream raw materials:

[4-(5-hydroxy-pentyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester

methanesulfonic acid 5-[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyl]-pentyl ester

C₁₉H₃₃NO₄