Sodium borohydride → HCID 54292500, compound

HRID 2247909Notes

Reaction equation

HRID 2247909 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[C:11]([CH:19]([O:22][CH3:23])[O:20][CH3:21])[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH3:21][O:20][CH:19]([O:22][CH3:23])[C:11]1[CH:10]=[C:9]([CH:1]([OH:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=[CH:13][C:12]=1[NH:15][C:16](=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19816038HCID 19816038, compound

Product 1

HCID 54292500HCID 54292500, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 25.6 parts of intermediate 65, namely N-[4-benzoyl-2-(dimethoxymethyl)phenyl]acetamide, in 119 parts of methanol were added portionwise 10.72 parts of sodium tetrahydroborate. Stirring was continued for a while at 60° C. and over weekend at room temperature. The reaction mixture was evaporated and the residue was taken up in water. The product was extracted with dichloromethane (2×) and the combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH3COOC2H5 /hexane 50:50→60:40). The eluent of the desired fraction was evaporated, yielding 13.1 parts (50.8%) of N-[2-(dimethoxymethyl)-4-(hydroxyphenylmethyl)phenyl]acetamide (interm. 66).

Workup

  1. waitwas continued for a while at 60° C. and over weekend at room temperature
  2. customThe reaction mixture was evaporated
  3. extractionThe product was extracted with dichloromethane (2×)
  4. customthe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CH3COOC2H5 /hexane 50:50→60:40)
  8. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-28ed86bd3a7645ebb01fd03631b0b774
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

Loading…