ChemicalBook CAS DataBase List ethyl 3-(dibenzylaMino)-2,2-difluoropropanoate

ethyl 3-(dibenzylaMino)-2,2-difluoropropanoate synthesis

5synthesis methods

Product Name:ethyl 3-(dibenzylaMino)-2,2-difluoropropanoate
CAS Number:541547-36-8
Molecular formula:C19H21F2NO2
Molecular Weight:333.37

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2H-Benzotriazole-2-methanamine, N,N-bis(phenylmethyl)-

121238-95-7
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N-((1H-benzo[d][1,2,3]triazol-1-yl)Methyl)-N-benzyl-1-phenylMethanaMine

57684-32-9
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ethyl 3-(dibenzylaMino)-2,2-difluoropropanoate

541547-36-8
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Yield:541547-36-8 99%

Reaction Conditions:

Stage #1: Ethyl bromodifluoroacetatewith chloro-trimethyl-silane;zinc in tetrahydrofuran at 20; for 0.166667 h;
Stage #2: 2H-1,2,3-benzotriazol-2-yl-N,N-dibenzylmethanamine;N-((1 H-benzo[d][1,2,3]triazol-1-yl)methyl)-N-benzyl-1-phenylmethanamine in tetrahydrofuran at 20; for 3 h;

Steps:

To a suspension of zinc powder (SIGMA-ALDRICH, 3.22 g, 49.2 mmol) in THF (96 mL), at rt, was added TMSCI (SIGMA-ALDRICH, 3.14 mL, 24.60 mmol). The mixture was stirred for 10 min and then ethyl bromodifluoroacetate (FLUOROCHEM, 3.48 mL, 27.1 mmol) was added. After stirring at rt for 10 min, a solution of mixture of 1 H- and 2H-1 ,2,3-benzotriazol-1-yl-N,N- dibenzylmethanamine (8.08 g, 24.60 mmol) in THF (27.3 mL) was added and the reaction mixture was stirred at rt for 3 h. A saturated solution of NaHCOs sat. was added, and the mixture was stirred for 15 min and filtered through a plug of Celite washing with EtOAc. Layers were separated, and the aqueous layer was extracted with EtOAc two times. The combined organic layers were dried, filtered and the solvent was removed in vacuo to obtain ethyl 3- (dibenzylamino)-2,2-difluoropropanoate (8.1 1 g, 99% yield). This material was used without further purification. NMR (300 MHz, CDCI₃) d ppm: 7.39-7.26 (m, 10H), 4.19 (q, J= 7.1 Hz, 2H), 3.70 (s, 4H), 3.16 (t, J= 13.1 Hz, 2H), 1.24 (t, J= 7.1 Hz, 3H).

References:

WO2019/145360,2019,A1 Location in patent:Page/Page column 37; 38

667-27-6
409 suppliers
$10.00/10g

57684-32-9
25 suppliers
$77.00/250mg

541547-36-8
32 suppliers
$122.00/100mg

References