Pyridine → 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl isopropylcarbamate

HRID 870700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870700
[CH3:1][C:2]1([CH3:17])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)[O:3]1.N1C=CC=CC=1.ClC(OC1C=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30]C=1)=O.C1C[O:40][CH2:39]C1>>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:17])([CH3:1])[O:3][B:4]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][O:16][C:39](=[O:40])[NH:34][CH:31]([CH3:30])[CH3:32])=[CH:13][CH:14]=2)[O:5]1

Komponenten

5

Edukt 4

HCID 1049PyridineHCID 8028Tetrahydrofuran2×HCID 821294-Nitrophenyl chloroformateHCID 114020504-(Hydroxymethyl)benzeneboronic acid pinacol ester

Produkt 1

HCID 866964024-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl isopropylcarbamate

Versuchsvorschrift

To a solution of [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanol (2.34 g, 10 mmol) and pyridine (890 ul, 11 mmol) in THF (50 ml) at rt was added dropwise a solution of 4-nitrophenyl chloroformate (2.22 g, 11 mmol) in THF (10 ml). The reaction mixture was stirred at rt for overnight. The precipitate was removed by filtration. The filtrate was concentrated to give the desired compound (4.2 g, may contain some pyridine HCl salt).

Aufarbeitung

  1. customThe precipitate was removed by filtration
  2. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-6023c19c56124c9f82c072db10e2be56
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969565B2

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