Triphenylphosphine → 4-(2-Morpholin-4-ylethoxy)benzeneboronic acid, pinacol ester

HRID 1907926Notes

Reaction equation

HRID 1907926 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.[N:17]1([CH2:23][CH2:24]O)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:24][CH2:23][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:11][CH:10]=2)[O:5]1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 611632-Morpholinoethanol2×HCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 5363146Diisopropyl azodicarboxylate2×

Product 1

HCID 46259104-(2-Morpholin-4-ylethoxy)benzeneboronic acid, pinacol esterYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-phenol (2.55 g, 11.58 mmol), 2-morpholin-4-ylethanol (1.60 mL, 1.73 g, 13.2 mmol) and triphenyl phosphine (3.64 g, 13.9 mmol) in methylene chloride (60 mL) at 0° C. was added dropwise DIAD (2.82 g, 13.9 mmol). The reaction was allowed to warm to room temperature and stir overnight. After 18 hours, additional portions of triphenyl phosphine (1.51 g, 5.8 mmol), 2-morpholin-4-ylethanol (0.70 mL, 5.8 mmol), and DIAD (1.17 g, 5.8 mmol) were added. After stirring an additional 2 hours at room temperature the reaction was concentrated and the residue purified by flash chromatography (5% to 25% EtOAc in CHCl3) to provide the product as a white solid (2.855 g, 74%).

Workup

  1. waitAfter 18 hours
  2. stirringAfter stirring an additional 2 hours at room temperature the reaction
  3. concentrationwas concentrated
  4. customthe residue purified by flash chromatography (5% to 25% EtOAc in CHCl3)

Sources & evidence

ORD record
ord-a465fcac59a9417ab5386e40676295d1
Source dataset
uspto-grants-2013_12
Patent number
US08598169B2

Reaction notes

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