ChemicalBook CAS DataBase List 1-Pyrrolidinecarboxylic acid, 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-2-yl]-, 1,1-dimethylethyl ester, (2S)-

1-Pyrrolidinecarboxylic acid, 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-2-yl]-, 1,1-dimethylethyl ester, (2S)- synthesis

6synthesis methods

Product Name:1-Pyrrolidinecarboxylic acid, 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-2-yl]-, 1,1-dimethylethyl ester, (2S)-
CAS Number:1613055-24-5
Molecular formula:C18H30BN3O4
Molecular Weight:363.26

1228552-62-2 Synthesis

(S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

1228552-62-2
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73183-34-3
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1-Pyrrolidinecarboxylic acid, 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-2-yl]-, 1,1-dimethylethyl ester, (2S)-

1613055-24-5
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Yield:1613055-24-5 85%

Reaction Conditions:

with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂;potassium acetate in N,N-dimethyl-formamide at 90; for 6 h;Inert atmosphere;Sealed tube;

Steps:

5.5 the preparation of compound 5-6

A mixture of compound 1-20 (0.36 g, 1.0 mmol), compound 1-14-2 (0.30 g, 1.2 mmol), Pd(dppf)Cl₂^'CH₂Cl₂ (40.8 mg, 0.05 mmol) and KOAc (0.25 g, 2.5 mmol) in DMF (5.0 mL) was stirred at 90 °C under N₂ for 6.0 hrs. After the reaction was completed, the mixture was cooled to rt, diluted with EtOAc (50 mL) and filtered through a celite pad. The filtrate was washed with water (30 mL x 3) and brine, dried over anhydrous Na₂S0₄ and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 1/2) to give the title compound (0.31 g, 85%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 364.5 [M+H]⁺; and NMR (400 MHz, CDC1₃) δ (ppm): 7.50 (s, 1H), 4.93-4.88 (m, 1H), 3.59-3.53 (m, 1H), 3.28-3.21 (m, 1H), 2.38-2.30 (m, 1H), 2.27-2.12 (m, 2H), 2.08-1.98 (m, 1H), 1.41 (s, 9H), 1.40-1.39 (m, 6H), 1.37-1.36 (m, 6H).

References:

WO2014/82380,2014,A1 Location in patent:Paragraph 00371; 00376