2-(Thiophen-2-ylmethyl)isoindoline-1,3-dione → HCID 4616003, compound

HRID 492227Notes

Reaction equation

HRID 492227 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17].[BH4-].[Na+]>CO>[OH:16][CH:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:17])[N:7]1[CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 33541542-(Thiophen-2-ylmethyl)isoindoline-1,3-dioneHCID 4311764Sodium borohydride

Product 1

HCID 4616003HCID 4616003, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 11 (700 mg, 2.88 mmol) in methanol (15 mL) at 0° C. was added sodium borohydride (164 mg, 4.32 mmol) and the resulting reaction mixture was allowed to stir at 0° C. for 2 hours. The reaction mixture was concentrated in vacuo to remove methanol and the residue was taken up in ethyl acetate and poured onto 1N HCl and extracted with ethyl acetate (3×30 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to provide 612 mg of 12 as a yellow solid (706 mg theoretical, 87% yield).

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove methanol
  4. additionpoured onto 1N HCl
  5. extractionextracted with ethyl acetate (3×30 mL)
  6. dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e04d2ed933b44138ae1246d4b06afbb9
Source dataset
uspto-grants-2009_05
Patent number
US07531671B2

Reaction notes

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