Sodium borohydride → HCID 19875845, compound

HRID 1886344Notes

Reaction equation

HRID 1886344 reaction equation
[CH3:1][CH:2]([CH3:18])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1)=[O:4].[BH4-].[Na+]>CO>[OH:4][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1)[CH:2]([CH3:18])[CH3:1]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19875874HCID 19875874, compound

Product 1

HCID 19875845HCID 19875845, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred and cooled (ice water, 10° C.) solution of 30 parts of intermediate 14, namely N-[4-(2-methyl-1-oxopropyl)-2-nitrophenyl]acetamide in 240 parts of methanol were added portionwise 4.5 parts of sodium tetrahydroborate. Upon completion, stirring was continued for 1 hour. The reaction mixture was evaporated and the residue was extracted with dichloromethane (3×104 parts). The combined extracts were washed with water, dried, filtered and evaporated, yielding 32 parts (100%) of N-[4-(1-hydroxy-2-methylpropyl)-2-nitrophenyl]acetamide (interm. 15).

Workup

  1. stirringUpon completion, stirring
  2. customThe reaction mixture was evaporated
  3. extractionthe residue was extracted with dichloromethane (3×104 parts)
  4. washThe combined extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2454780b224d4b35acfe35dc4a5e3dbe
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

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