3-Methoxybenzaldehyde → HCID 18172426, compound

HRID 397069Notes

Reaction equation

HRID 397069 reaction equation
[CH2:1]([NH:8][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:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH2:1]([N:8]([CH2:25][C:24]1[CH:27]=[CH:28][CH:29]=[C:22]([O:21][CH3:20])[CH:23]=1)[CH2:9][CH:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 115693-MethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 130729052-(Benzylamino)-1-(4-methoxyphenyl)ethan-1-ol

Product 1

HCID 18172426HCID 18172426, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Alternatively, to a solution of 2-benzylamino-1-(4-methoxy-phenyl)-ethanol (1.20 g, 4.66 mmol, see Preparation 61) and 3-methoxybenzaldehyde (0.700 g, 5.13 mmol) in 1,2 DCE (25 ml) was added NaB(OAc)3H. The mixture was stirred at RT overnight. The reaction mixture was poured into sat. NaHCO3 (30 ml) and extracted with CH2Cl2 (3×50 ml). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified via flash chromatography (Biotage 15% EtOAc/hexanes) to give the title product (1.72 g, 4.56 mmol, 98% yield).

Workup

  1. extractionextracted with CH2Cl2 (3×50 ml)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via flash chromatography (Biotage 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-783d884fa0304b45886a75c86afa9b3a
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

Loading…