Potassium fluoride, 99%, spray-dried → HCID 66981871, compound

HRID 1942715Notes

Reaction equation

HRID 1942715 reaction equation
[CH2:1]([C:3]1[C:8]([B:9]2[O:13]C(C)(C)C(C)(C)[O:10]2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:18][N:19]1[CH2:22][CH:21]([C:23]([O:25][CH3:26])=[O:24])[CH2:20]1)[CH3:2].F.[K]>CO>[CH2:1]([C:3]1[C:4]([CH2:18][N:19]2[CH2:22][CH:21]([C:23]([O:25][CH3:26])=[O:24])[CH2:20]2)=[CH:5][CH:6]=[CH:7][C:8]=1[B:9]([OH:10])[OH:13])[CH3:2]

Participants

4

Reactant 2

HCID 53443437Potassium fluoride, 99%, spray-driedHCID 66981730Methyl 1-(2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)azetidine-3-carboxylate

Product 1

HCID 66981871HCID 66981871, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-{[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}-3-azetidinecarboxylate (5.23 g, 14.56 mmol) in Methanol (50 mL) was added potassium hydrogen fluoride (16.17 mL, 72.8 mmol). The mixture was stirred at rt for an hour. LCMS showed that the starting material was consumed completely. The solvent was removed under the reduced pressure and the residue was acidified with HCl (1.0 M) to pH value around 3 then extracted with EtOAc (50 mL). The aqueous phase was adjusted to pH value around 6 with sat. NaHCO3 solution, the target product was collected by filtering and dried in vacuum to give (2-ethyl-3-((3-(methoxycarbonyl)azetidin-1-yl)methyl)phenyl)boronic acid (2.5 g) as a brown solid. δH (DMSO-d6, 600 MHz): 1.02 (2H, m), 2.81 (2H, m), 3.70 (4H, m), 4.23 (4H, m), 4.33 (2H, m), 7.00 (2H, m), 7.43 (1H, m), 9.93 (1H, m).

Workup

  1. customwas consumed completely
  2. customThe solvent was removed under the reduced pressure
  3. extractionthen extracted with EtOAc (50 mL)
  4. customthe target product was collected
  5. filtrationby filtering
  6. customdried in vacuum

Sources & evidence

ORD record
ord-2cff130d33bc4480938e408399a5bfa3
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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