tert-Butyl piperazine-1-carboxylate → (3-((4-(Tert-butoxycarbonyl)piperazin-1-yl)methyl)phenyl)boronic acid

HRID 662073Notes

Reaction equation

HRID 662073 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([B:9]([OH:11])[OH:10])[CH:6]=[CH:7][CH:8]=1)=O.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:24][C:21]([O:20][C:18]([N:12]1[CH2:17][CH2:16][N:15]([CH2:1][C:3]2[CH:4]=[C:5]([B:9]([OH:11])[OH:10])[CH:6]=[CH:7][CH:8]=2)[CH2:14][CH2:13]1)=[O:19])([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27343563-Formylphenylboronic acidHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 42609723(3-((4-(Tert-butoxycarbonyl)piperazin-1-yl)methyl)phenyl)boronic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of (3-formylphenyl)boronic acid (3.0 g, 20.0 mmol) in DCM (100 mL) was added 1,1-dimethylethyl 1-piperazinecarboxylate (3.91 g, 21.0 mmol), and NaBH(OAc)3 (6.36 g, 30.0 mmol), and the mixture stirred at room temperature for 17 h. The organic layer was diluted with EtOAc (100 mL), washed with H2O (30 mL), dried over Na2SO4, filtered and concentrated to afford 7.72 g (quantitative) of the title compound. LC-MS m/z 321 (M+H)+.

Workup

  1. washwashed with H2O (30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fc169c5cc1de47bfadfcf8178133a3fe
Source dataset
uspto-grants-2011_12
Patent number
US08084449B2

Reaction notes

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