Sodium borohydride → HCID 23354004, compound

HRID 235270Notes

Reaction equation

HRID 235270 reaction equation
[C:1]([C:4]1[S:24][C:7]2[CH2:8][CH2:9][CH:10]3[C:15]([C:6]=2[CH:5]=1)=[N:14][N:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)[C:12](=[O:23])[CH2:11]3)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[S:24][C:7]2[CH2:8][CH2:9][CH:10]3[C:15]([C:6]=2[CH:5]=1)=[N:14][N:13]([C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=1)[C:12](=[O:23])[CH2:11]3)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22067878HCID 22067878, compound

Product 1

HCID 23354004HCID 23354004, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1.3 g of 8-acetyl-4,4a, 5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one in methanol was added 300 mg of sodium borohydride under ice-cooling and the mixture was stirred for 3 hours. The mixture was concentrated in vacuo until about a half volume of the methanol was evaporated and water was added, and then extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel (SiO2 :30 g) column using a mixed solvent of chloroform and methanol (98:2) as an eluent. The resulting solid was recrystallized from a mixed solvent of ethyl acetate and hexane to give 570 mg of 8-(1-hydroxyethyl)-4,4a,5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one as a pale yellow powder, melting at 129°-145° C.

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated in vacuo until about a half volume of the methanol
  3. customwas evaporated
  4. additionwater was added
  5. extractionextracted with chloroform
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on a silica gel (SiO2 :30 g) column
  10. customThe resulting solid was recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-b2d0cb46dd9241d199afd875f5209986
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

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