(1R)-N-[(E)-1-ethoxycarbonyl-2,2,2-trifluoroethylidene]-(2-tert-butyldimethylsilyloxy-1-phenylethyl)amine

Base Information

• Chemical Name: (1R)-N-[(E)-1-ethoxycarbonyl-2,2,2-trifluoroethylidene]-(2-tert-butyldimethylsilyloxy-1-phenylethyl)amine
• CAS No.: 921224-73-9
• Molecular Formula: C₁₉H₂₈F₃NO₃Si
• Molecular Weight: 403.517
• Mol file: 921224-73-9.mol

Synonyms:(1R)-N-[(E)-1-ethoxycarbonyl-2,2,2-trifluoroethylidene]-(2-tert-butyldimethylsilyloxy-1-phenylethyl)amine

Chemical Property of (1R)-N-[(E)-1-ethoxycarbonyl-2,2,2-trifluoroethylidene]-(2-tert-butyldimethylsilyloxy-1-phenylethyl)amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-N-[(E)-1-ethoxycarbonyl-2,2,2-trifluoroethylidene]-(2-tert-butyldimethylsilyloxy-1-phenylethyl)amine

There total 1 articles about (1R)-N-[(E)-1-ethoxycarbonyl-2,2,2-trifluoroethylidene]-(2-tert-butyldimethylsilyloxy-1-phenylethyl)amine 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: 92.0%

ethyl-3,3,3-trifluoropyruvate (13081-18-0) + (1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethanamine (120417-13-2,120666-55-9) → (1R)-N-[(E)-1-ethoxycarbonyl-2,2,2-trifluoroethylidene]-(2-tert-butyldimethylsilyloxy-1-phenylethyl)amine (921224-73-9)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1039/c0ob00424c

Reference yield:

(1R)-N-[(E)-1-ethoxycarbonyl-2,2,2-trifluoroethylidene]-(2-tert-butyldimethylsilyloxy-1-phenylethyl)amine (921224-73-9) → (3S,5R)-3-propyl-3-trifluoromethyl-5-phenylmorpholin-2-one (921224-79-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SnCl₄ / CH₂Cl₂ / 20 °C

1.2: TBAF / tetrahydrofuran / 0 - 20 °C

2.1: 90 percent / hydrogen; trifluoroacetic acid / Pd(OH)2/C / methanol / 20 °C / 3000.24 Torr

With hydrogen; tin(IV) chloride; trifluoroacetic acid; palladium dihydroxide; In methanol; dichloromethane;

DOI:10.1021/ol062593+

Reference yield:

(1R)-N-[(E)-1-ethoxycarbonyl-2,2,2-trifluoroethylidene]-(2-tert-butyldimethylsilyloxy-1-phenylethyl)amine (921224-73-9) + allyl-trimethyl-silane (762-72-1) → (3R,5R)-3-allyl-5-phenyl-3-(trifluoromethyl)morpholin-2-one + (3S,5R)-3-allyl-3-trifluoromethyl-5-phenylmorpholin-2-one (921224-77-3)

Guidance literature:

(1R)-N-[(E)-1-ethoxycarbonyl-2,2,2-trifluoroethylidene]-(2-tert-butyldimethylsilyloxy-1-phenylethyl)amine; allyl-trimethyl-silane; With tin(IV) chloride; In dichloromethane; at 20 ℃;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol062593+

upstream raw materials:

ethyl-3,3,3-trifluoropyruvate

(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethanamine

Downstream raw materials:

(3S,5R)-3-allyl-3-trifluoromethyl-5-phenylmorpholin-2-one

(3S,5R)-3-propyl-3-trifluoromethyl-5-phenylmorpholin-2-one

(S)-3,3,3-trifluoro-2-(((R)-2-hydroxy-1-phenylethyl)amino)propan-1-ol

2-((1R)-2-hydroxy-1-phenylethylamino)-3,3,3-trifluoropropan-1-ol