Water → HCID 53238283, compound

HRID 2371031Notes

Reaction equation

HRID 2371031 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][O:6][CH:5]([C:10]3([NH:13][C:14](=O)OCC)[CH2:12][CH2:11]3)[C:4]=2[CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[CH2:26]1[CH2:30]OC[CH2:27]1>>[S:1]1[C:9]2[CH2:8][CH2:7][O:6][CH:5]([C:10]3([NH:13][CH3:14])[CH2:12][CH2:11][CH2:30][CH2:26][CH2:27]3)[C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 68334732HCID 68334732, compound

Product 1

HCID 53238283HCID 53238283, compoundYield 84%

Procedure

To a solution of ethyl 1-(6,7-dihydro-4H-thieno[3,2-c]pyran-4-yl)cyclopropylcarbamate (1.1 g, 4.1 mmol) in dry THF (20 mL) at 0° C. under N2 was added LiAlH4 (152 mg, 4.0 mmol) in one portion. The resulting mixture was refluxed for 2 h and then cooled to room temperature. Water (5 mL) was added to quench the reaction. The reaction mixture was filtered and the filtrate was extracted with EtOAc (3×75 mL). The combined extract was washed with brine, and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (700 mg, 84%).

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. customto quench
  3. customthe reaction
  4. filtrationThe reaction mixture was filtered
  5. extractionthe filtrate was extracted with EtOAc (3×75 mL)
  6. extractionThe combined extract
  7. washwas washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationAfter filtration and concentration
  10. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-a2013aaf78c74eda8a677d123d2c4839
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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