(2E)-2-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene]-2-fluoro-N-(2-phenylethyl)ethanamide

Base Information

• Chemical Name: (2E)-2-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene]-2-fluoro-N-(2-phenylethyl)ethanamide
• CAS No.: 603962-90-9
• Molecular Formula: C₂₂H₃₄FNO₂Si
• Molecular Weight: 391.601
• Mol file: 603962-90-9.mol

Synonyms:(2E)-2-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene]-2-fluoro-N-(2-phenylethyl)ethanamide

Chemical Property of (2E)-2-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene]-2-fluoro-N-(2-phenylethyl)ethanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E)-2-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene]-2-fluoro-N-(2-phenylethyl)ethanamide

There total 2 articles about (2E)-2-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene]-2-fluoro-N-(2-phenylethyl)ethanamide 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: 87.0%

phenethylamine (64-04-0) + (2E)-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene](fluoro)ethanoic acid (603962-82-9) → (2E)-2-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene]-2-fluoro-N-(2-phenylethyl)ethanamide (603962-90-9)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 4h;

DOI:10.1016/S0040-4039(03)01542-9

Reference yield:

2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>cyclopentanone (129600-97-1) → (2E)-2-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene]-2-fluoro-N-(2-phenylethyl)ethanamide (603962-90-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / diethyl ether / 0.08 h / -5 °C

1.2: 33 percent / Wadsworth-Horner-Emmons reagent / diethyl ether / 4 h

2.1: 97 percent / aq. KOH / methanol / 8 h / 20 °C

3.1: diisopropylethylamine; TBTU / CH₂Cl₂ / 0.08 h

3.2: 87 percent / CH₂Cl₂ / 3 h

With potassium hydroxide; sodium hydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/jm0495982

Reference yield:

(2E)-2-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene]-2-fluoro-N-(2-phenylethyl)ethanamide (603962-90-9) → {2-[2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentylidene]-2-fluoro-ethyl}-phenethyl-amine (603962-96-5)

Guidance literature:

(2E)-2-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene]-2-fluoro-N-(2-phenylethyl)ethanamide; With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In dichloromethane; at 0 ℃; for 2h;

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃;

DOI:10.1016/S0040-4039(03)01542-9

upstream raw materials:

phenethylamine

(2E)-[(2R,S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentylidene](fluoro)ethanoic acid

2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>cyclopentanone

Downstream raw materials:

{2-[2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentylidene]-2-fluoro-ethyl}-phenethyl-amine

[2-(2-cyano-cyclopentylidene)-2-fluoro-ethyl]-phenethyl-carbamic acid tert-butyl ester

[2-fluoro-2-(2-hydroxymethyl-cyclopentylidene)-ethyl]-phenethyl-carbamic acid tert-butyl ester

(1R,S)-(2E)-2-{2-[(tert-butoxycarbonyl)(2-phenylethyl)amino]-1-fluoroethylidene}cyclopentanecarboxylic acid