(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethanamine

Base Information

• Chemical Name: (1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethanamine
• CAS No.: 611210-24-3
• Molecular Formula: C₁₈H₂₇NO₃
• Molecular Weight: 305.417
• Mol file: 611210-24-3.mol

Synonyms:(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethanamine

Chemical Property of (1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethanamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethanamine

There total 7 articles about (1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethanamine 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: 81.0%

N-((1S)-2-(4-(cyclohexylmethoxy)phenyl)-1-(2,5-dioxolanyl)ethyl)(benzyloxy)formamide (611210-12-9) → (1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethanamine (611210-24-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 18h; atmospheric pressure;

DOI:10.1016/j.bmc.2003.09.031

Reference yield:

N-(benzyloxycarbonyl)-L-tyrosine methyl ester (13512-31-7) → (1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethanamine (611210-24-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / K₂CO₃ / dimethylformamide / 18 h / 20 °C

2: 42 percent / LiCl; NaBH₄ / tetrahydrofuran; ethanol / 18 h / 20 °C

3: 83 percent / ethyldiisopropylamine; SO₃/pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / cooling

4: 48 percent / pyridinium tosylate / toluene / 18 h / 80 °C

5: 81 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / atmospheric pressure

With pyridine; sodium tetrahydroborate; sulfur trioxide; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2003.09.031

Reference yield:

L-tyrosine methyl ester HCl (3417-91-2) → (1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethanamine (611210-24-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / Et₃N / tetrahydrofuran / 18 h / 20 °C

2: 77 percent / K₂CO₃ / dimethylformamide / 18 h / 20 °C

3: 42 percent / LiCl; NaBH₄ / tetrahydrofuran; ethanol / 18 h / 20 °C

4: 83 percent / ethyldiisopropylamine; SO₃/pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / cooling

5: 48 percent / pyridinium tosylate / toluene / 18 h / 80 °C

6: 81 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / atmospheric pressure

With pyridine; sodium tetrahydroborate; sulfur trioxide; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2003.09.031

upstream raw materials:

N-((1S)-2-(4-(cyclohexylmethoxy)phenyl)-1-(2,5-dioxolanyl)ethyl)(benzyloxy)formamide

N-(benzyloxycarbonyl)-L-tyrosine methyl ester

L-tyrosine methyl ester HCl

N-(benzyloxycarbonyl)-O-cyclohexylmethyl-L-tyrosinal

Downstream raw materials:

(2S)-N-{(1S)-2-[4-(cyclohexylmethoxy)phenyl]-1-(1,3-dioxolan-2-yl)ethyl}-2-hydroxy-4-methylpentanamide