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ChemicalBook CAS DataBase List DIMETHYL-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE
909391-56-6

DIMETHYL-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE synthesis

2synthesis methods
-

Yield: 77%

Reaction Conditions:

with potassium carbonate in acetonitrile at 20; for 16 h;

Steps:

XI
Procedure Xl INTERMEDIATE XI.1 : Dimethyl-r3-(4,4,5,5-tetramethyl-ri ,3,21-dioxaborolan-2- vDbenzyllamineTo a solution of 3-bromomethylphenyl boronic acid pinacol ester (Combi Block Inc., 297 mg, 1.0 mmol) in acetonitrile (5 ml.) was added dimethylamine (2M solution in methanol, EPO 2.0 mmol) followed by the addition of K2CO3 (691 nng, 5.0 mmol). The reaction mixture was stirred at room temperature for 16 h. Acetonitrile was removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated NaHCO3, dried (MgSO4), filtered and the filtrate concentrated in vacuo to g ive dimethyl-[3-(4, 4, 5, 5-tetramethyl[1 , 3, 2]dioxaborolan-2-yl)benzyl]amine(INTERMEDIATE XU) as a viscous oil (200 mg, 0.77 mmol, 77%). Data for dimethyl-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]amine(INTERMEDIATE Xl.1): 1H NMR (300 MHz, CD3OD): δ 7.70 (m, 2H), 7.30-7.45 (m, 2H), 3.50 (s, 2H), 2.28 (s, 6H), 1.36 (s, 12H) ppm; MS (ESI), m/z: 262 ([M+H]+).

References:

AKZO NOBEL N.V.;PHARMACOPEIA DRUG DISCOVERY, INC. WO2006/95014, 2006, A1 Location in patent:Page/Page column 43-44

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