Sodium borohydride → HCID 58399574, compound

HRID 889496Notes

Reaction equation

HRID 889496 reaction equation
[CH2:1]([O:3][C:4]1[C:12]2[C:11](=[O:13])[N:10]([C:14]3[C:19]([F:20])=[CH:18][C:17]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][C:15]=3[F:27])[C:9](=[O:28])[C:8]=2[C:7]([O:29][CH2:30][CH3:31])=[C:6]2[CH:32]=[CH:33][CH:34]=[CH:35][C:5]=12)[CH3:2].[BH4-].[Na+]>C1COCC1.CO>[CH2:30]([O:29][C:7]1[C:8]2[C:9](=[O:28])[N:10]([C:14]3[C:15]([F:27])=[CH:16][C:17]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][C:19]=3[F:20])[CH:11]([OH:13])[C:12]=2[C:4]([O:3][CH2:1][CH3:2])=[C:5]2[CH:35]=[CH:34][CH:33]=[CH:32][C:6]=12)[CH3:31]

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 58399563HCID 58399563, compound

Product 1

HCID 58399574HCID 58399574, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl {4-[4,9-bis(ethyloxy)-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3,5-difluorophenyl}acetate (0.240 g, 0.50 mmol) in THF (10 ml) and methanol (5 ml) was added sodium borohydride (0.019 g, 0.50 mmol) slowly under an argon atmosphere. This was stirred at room temperature for 15 minutes, and then a further 0.057 g (1.50 mmol) of sodium borohydride was added to drive the reaction to completion. After 1.5 hours the reaction was evaporated and quenched with an aqueous solution of ammonium chloride. This was extracted ×2 with ethyl acetate (25 ml) and the combined extracts washed with brine. The organics layer was then dried over magnesium sulphate, filtered and evaporated to give the title compound as a yellow oily solid (0.240 g, 0.49 mmol) LC/MS: Rt=3.42 and 3.46, [MH]+ 486.

Workup

  1. customthe reaction to completion
  2. customAfter 1.5 hours the reaction was evaporated
  3. customquenched with an aqueous solution of ammonium chloride
  4. extractionThis was extracted ×2 with ethyl acetate (25 ml)
  5. washthe combined extracts washed with brine
  6. dry with materialThe organics layer was then dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-0faefda98e524d2282665364cb613800
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

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