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

Base Information

• Chemical Name: trans-(4-formylcyclohexyl)methylcarbamic acid tert-butyl ester
• CAS No.: 400898-94-4
• Molecular Formula: C₁₃H₂₃NO₃
• Molecular Weight: 241.331
• Mol file: 400898-94-4.mol

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

Chemical Property of trans-(4-formylcyclohexyl)methylcarbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-(4-formylcyclohexyl)methylcarbamic acid tert-butyl ester

There total 6 articles about trans-(4-formylcyclohexyl)methylcarbamic 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: 100.0%

trans-N-[4-(N-methoxy-N-methylcarbamoyl)cyclohexyl]-N-methylcarbamic acid tert-butyl ester (400898-93-3) → trans-(4-formylcyclohexyl)methylcarbamic acid tert-butyl ester (400898-94-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -50 - 15 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/jm300256z

Reference yield:

tert-butyl ((1r,4r)-4-(hydroxymethyl)cyclohexyl)(methyl)carbamate (400899-08-3) → trans-(4-formylcyclohexyl)methylcarbamic acid tert-butyl ester (400898-94-4)

Guidance literature:

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

DOI:10.2533/000942905777676858

Reference yield:

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid (53292-90-3,130309-46-5,53292-89-0) → trans-(4-formylcyclohexyl)methylcarbamic acid tert-butyl ester (400898-94-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / carbonyldiimidazole / 20 °C

2: NaH / dimethylformamide / 0 - 20 °C

3: LiBH₄ / tetrahydrofuran / Heating

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

With lithium borohydride; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4: Swern oxidation;

DOI:10.2533/000942905777676858

upstream raw materials:

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

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

methyl (1r,4r)‐4‐{[(tert‐butoxy)carbonyl](methyl)amino}cyclohexane‐1‐carboxylate

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid

Downstream raw materials:

C₁₇H₂₉NO₄

trans-[4-(2,2-dibromovinyl)cyclohexyl]-N-methylcarbamic acid tert-butyl ester

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

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