Water → HCID 10000127, compound

HRID 1241532Notes

Reaction equation

HRID 1241532 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[O:5][C:6]1[C:7]([CH:15]=[O:16])=[C:8]([CH3:14])[NH:9][C:10](=[O:13])[C:11]=1[I:12].[BH4-].[Na+].O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:20][C:18]1[CH:17]=[C:4]([CH:3]=[C:2]([CH3:1])[CH:19]=1)[O:5][C:6]1[C:7]([CH2:15][OH:16])=[C:8]([CH3:14])[NH:9][C:10](=[O:13])[C:11]=1[I:12]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 21935306HCID 21935306, compound

Product 1

HCID 10000127HCID 10000127, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of compound 269 (500 mg; 1.3 mmol) in methanol (50 ml) was added NaBH4 (350 mg; 9.2 mmol) in small portions for a period of 10 min. After 1 hour on stirring at room temperature, water (20 ml) and a solution 10% potassium carbonate (30 ml) were added. The mixture was extracted with ethyl acetate (3×60 ml) and the organic layer was washed with brine, dried over magnesium sulfate and the solvent was removed under reduced pressure giving colorless microcrystals which correspond to the titled compound (490 mg; 97%) m.p.=248–250° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×60 ml)
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customgiving colorless microcrystals which

Sources & evidence

ORD record
ord-969a48ac587d488884983effa8c179fc
Source dataset
uspto-grants-2006_10
Patent number
US07115608B2

Reaction notes

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