{1Z,1[2S,2(1R)]}-{2-[1-(4-bromophenyl)-1-hydroxymethyl]methylcyclohexylidene}methyl N,N-diisopropylcarbamate

Base Information

• Chemical Name: {1Z,1[2S,2(1R)]}-{2-[1-(4-bromophenyl)-1-hydroxymethyl]methylcyclohexylidene}methyl N,N-diisopropylcarbamate
• CAS No.: 804566-50-5
• Molecular Formula: C₂₂H₃₂BrNO₃
• Molecular Weight: 438.405
• Mol file: 804566-50-5.mol

Synonyms:{1Z,1[2S,2(1R)]}-{2-[1-(4-bromophenyl)-1-hydroxymethyl]methylcyclohexylidene}methyl N,N-diisopropylcarbamate

Chemical Property of {1Z,1[2S,2(1R)]}-{2-[1-(4-bromophenyl)-1-hydroxymethyl]methylcyclohexylidene}methyl N,N-diisopropylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {1Z,1[2S,2(1R)]}-{2-[1-(4-bromophenyl)-1-hydroxymethyl]methylcyclohexylidene}methyl N,N-diisopropylcarbamate

There total 3 articles about {1Z,1[2S,2(1R)]}-{2-[1-(4-bromophenyl)-1-hydroxymethyl]methylcyclohexylidene}methyl N,N-diisopropylcarbamate 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-bromo-benzaldehyde (1122-91-4) + (2-methyl-1-cyclohexenyl)methyl N,N-diisopropylcarbamate (432555-24-3) → {1Z,1[2R,2(1S)]}-{2-[1-(4-bromophenyl)-1-hydroxymethyl]methylcyclohexylidene}methyl N,N-diisopropylcarbamate + {1Z,1[2S,2(1R)]}-{2-[1-(4-bromophenyl)-1-hydroxymethyl]methylcyclohexylidene}methyl N,N-diisopropylcarbamate (804566-50-5)

Guidance literature:

(2-methyl-1-cyclohexenyl)methyl N,N-diisopropylcarbamate; With n-butyllithium; (-)-sparteine; In hexane; toluene; at -78 ℃; for 0.166667h;

With titanium tris(diethylamido)chloride; In hexane; toluene; at -78 ℃; for 2h;

4-bromo-benzaldehyde; In hexane; toluene; at -78 - 20 ℃; Title compound not separated from byproducts;

DOI:10.1002/ejoc.200500283

Reference yield:

N,N-diisopropylcarbamoyl chloride (19009-39-3) → {1Z,1[2S,2(1R)]}-{2-[1-(4-bromophenyl)-1-hydroxymethyl]methylcyclohexylidene}methyl N,N-diisopropylcarbamate (804566-50-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / NaH / tetrahydrofuran; hexane / 16 h / Heating

2.1: sec-BuLi; TMEDA; (-)-sparteine / toluene / -78 °C

2.2: Ti(OiPr)3 / toluene / -78 °C

2.3: toluene / -78 - 20 °C

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; sodium hydride; (-)-sparteine; In tetrahydrofuran; hexane; toluene;

DOI:10.1002/1099-0690(20022)2002:3<414::aid-ejoc414>3.0.co;2-2

Reference yield:

(2-methylcyclohex-1-en-1yl)methanol (29474-11-1) → {1Z,1[2S,2(1R)]}-{2-[1-(4-bromophenyl)-1-hydroxymethyl]methylcyclohexylidene}methyl N,N-diisopropylcarbamate (804566-50-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / NaH / tetrahydrofuran; hexane / 16 h / Heating

2.1: sec-BuLi; TMEDA; (-)-sparteine / toluene / -78 °C

2.2: Ti(OiPr)3 / toluene / -78 °C

2.3: toluene / -78 - 20 °C

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; sodium hydride; (-)-sparteine; In tetrahydrofuran; hexane; toluene;

DOI:10.1002/1099-0690(20022)2002:3<414::aid-ejoc414>3.0.co;2-2

upstream raw materials:

4-bromo-benzaldehyde

(2-methyl-1-cyclohexenyl)methyl N,N-diisopropylcarbamate

N,N-diisopropylcarbamoyl chloride

(2-methylcyclohex-1-en-1yl)methanol