Water → HCID 18172426, compound

HRID 397068Notes

Reaction equation

HRID 397068 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO>[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[CH2:9][CH:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 18172428HCID 18172428, compound

Product 1

HCID 18172426HCID 18172426, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[benzyl-(3-methoxy-benzyl)-amino]-1-(4-methoxy-phenyl)-ethanone (13.8 g, 36.75 mmol, see Preparation 62) in MeOH (150 ml) cooled to 0° C. was added NaBH4 in five equal portions over 30 minutes. The reaction was stirred overnight while slowly warming to RT. Water (100 ml) was added to the reaction mixture, the volume was reduced by half in vacuo, and the mixture extracted with CH2Cl2 (3×100 ml). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography of the residue (SiO2, gradient elution 20%-50% EtOAc/hexanes) gave the title product (12.87 g, 34.1 mmol, 93% yield).

Workup

  1. extractionthe mixture extracted with CH2Cl2 (3×100 ml)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washFlash chromatography of the residue (SiO2, gradient elution 20%-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-728e5adfc21f49d8b9cb3012c11e6b42
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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