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

HRID 870700Notes

Reaction equation

HRID 870700 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-6023c19c56124c9f82c072db10e2be56
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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