Pyrrolidine → [2-Chloro-5-(pyrrolidin-1-ylmethyl)phenyl]boronic acid

HRID 537033Notes

Reaction equation

HRID 537033 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][C:3]=1[B:10]([OH:12])[OH:11].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][C:3]=1[B:10]([OH:12])[OH:11]

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 27632392-Chloro-5-formylphenylboronic acidHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66747873[2-Chloro-5-(pyrrolidin-1-ylmethyl)phenyl]boronic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (2-chloro-5-formylphenyl)boronic acid (1.00 g, 5.42 mmol) in DCM (30 mL) were added pyrrolidine (0.45 mL, 5.42 mmol) and sodium triacetoxyborohydride (2.39 g, 11.3 mmol). The reaction mixture was allowed to stir at rt for 2.5 h and then diluted with brine. The mixture was extracted with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated to give [2-chloro-5-(pyrrolidin-1-ylmethyl)phenyl]boronic acid.

Workup

  1. extractionThe mixture was extracted with DCM
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f2214d6bb2194815b2db25e1c7207bc7
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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