ChemicalBook CAS DataBase List N-((R)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propanaMide

N-((R)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propanaMide synthesis

10synthesis methods

Product Name:N-((R)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propanaMide
CAS Number:1005450-55-4
Molecular formula:C22H20F3NO
Molecular Weight:371.4

2-PropenaMide, N-[(1R)-1-(1-naphthalenyl)ethyl]-3-[3-(trifluoroMethyl)phenyl]-, (2E)-

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N-((R)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propanaMide

1005450-55-4
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$72.00/250mg

Yield: 91.2%

Reaction Conditions:

with hydrogen;palladium on activated carbon in methanol;toluene at 20; for 1.5 h;Product distribution / selectivity;

Steps:

2
hi yet another variation, the reduction of the double bond and amide carbonyl of (E)-N-((i?)-l-naphthalen-l-yl-ethyl)-3-(3-trifluoromethyl-phenyl)-acrylamide is carried out in a stepwise manner. Either the carbonyl group or the alkene double bond can be reduced first. For example, the reduction of the alkene double bond is achieved by hydrogenation in the presence of a metal catalyst.[0123] A suspension of (E)-N-((i?)-l-naphthalen-l-yl-ethyl)-3-(3-trifluoromethyl-phenyl)- acrylamide (1.0 equiv.; 0.67 mmol; 250 mg) and Pd/C 10 wt% (25 mg) was stirred in a mixture of methanol and toluene (7 mL/lmL). The reaction flask was evacuated and back filled using a hydrogen filled balloon (three times). The reaction mixture is stirred at room temperature and the progress of the reaction was monitored using high performance liquid chromatography. After 90 minutes, the reaction mixture was filtered over a bed of celite and the solvent from the filtrate was removed in vacuo. The resulting solid was dried overnight at 45⁰C using a vacuum oven. Isolated yield: 91.2% (229 mg). The identity of the amide was confirmed by ¹H NMR and mass spectrometry. (400MHz, CDCl₃) δ ppm 1.60 (d, 3H) 2.39- 2.53 (m, 2H) 2.96-3.13 ( m, 2H) 5.55 (br. S., IH) 5.87-5.96 (m, IH) 7.29-7.38 (m, 2H) 7.39- 7.46 (m, 4H) 7.46-7.55 (m, 2H) 7.76-7.82 (m, IH) 7.83-7.89 (m, IH) 8.00-8.07 (m, IH) and HRMS (M+l): 372.1

References:

AMGEN INC. WO2009/2427, 2008, A2 Location in patent:Page/Page column 39

3886-70-2 Synthesis