ChemicalBook CAS DataBase List Carbamic acid, N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]-, 1,1-dimethylethyl ester

Carbamic acid, N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]-, 1,1-dimethylethyl ester synthesis

4synthesis methods

Product Name:Carbamic acid, N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]-, 1,1-dimethylethyl ester
CAS Number:1171897-03-2
Molecular formula:C19H30BNO4
Molecular Weight:347.26

(S)-[1-(4-BROMO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER

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Carbamic acid, N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]-, 1,1-dimethylethyl ester

1171897-03-2
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Yield:1171897-03-2 99%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane at 90; for 2 h;Temperature;

Steps:

1 Exemplary Synthesis of Exemplary Compound 167 Step 1

To a solution of tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]carbamate (5 g, 16.7 mmol, 1 eq) and 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (5.08 g, 20.0 mmol, 1.2 eq) in dioxane (100 mL) was added [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (975 mg, 1.33 mmol, 0.08 eq) and potassium acetate (3.27 g, 33.31 mmol, 2 eq).
The mixture was stirred at 90° C. for 2 hours.
The reaction mixture was concentrated to give crude product.
The crude product was purified by silica gel chromatography (petroleum ether:ethyl acetate=1:0 to 10:1).
Compound tert-butyl N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate (8.2 g, 16.44 mmol, 99% yield) was obtained as a yellow oil.

References:

US2019/300521,2019,A1 Location in patent:Paragraph 1203-1205

24424-99-5 Synthesis