Benzaldehyde → (5-Benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

HRID 15577

Reaction equation

HRID 15577 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:23]([O:27][C:28](=[O:43])[CH2:29][N:30]1[C:34]2[CH:35]=[CH:36][C:37]([NH2:39])=[CH:38][C:33]=2[N:32]=[C:31]1[CH2:40][CH2:41][CH3:42])([CH3:26])([CH3:25])[CH3:24]>ClCCCl.O>[C:23]([O:27][C:28](=[O:43])[CH2:29][N:30]1[C:34]2[CH:35]=[CH:36][C:37]([NH:39][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:38][C:33]=2[N:32]=[C:31]1[CH2:40][CH2:41][CH3:42])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67200153(5-Amino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

Product 1

HCID 67200053(5-Benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

Sodium triacetoxyborohydride (1.8 g, 8.4 mmol) was added to a solution of benzaldehyde (0.68 mL, 6.5 mmol) and (5-amino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester (1.8 g, 6.5 mmol) in DCE (15 mL), and stirred overnight at room temperature. The reaction solution was diluted with H2O. The organic solution was washed with brine, dried over MgSO4, and concentrated to afford the subtitle compound that was used without further purification. MS calculated for C23H29N3O2+H: 380, observed: 380.

Workup

  1. washThe organic solution was washed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eb1c7c4fd0b249119a8169ad059af745
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Linked notes

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