Tetrahydrofuran → HCID 19605215, compound

HRID 1603491Notes

Reaction equation

HRID 1603491 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.O1CCCC1.C([O:24][C:25]([C:27]1[S:31][C:30]2=[CH:32][N:33]=[C:34]([C:35](OCC)=[O:36])[N:29]2[CH:28]=1)=O)C>CO>[OH:24][CH2:25][C:27]1[S:31][C:30]2=[CH:32][N:33]=[C:34]([CH2:35][OH:36])[N:29]2[CH:28]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 19605166HCID 19605166, compoundHCID 21273587HCID 21273587, compound

Product 1

HCID 19605215HCID 19605215, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-78 °C

Procedure

A 9.4 ml portion of a 1.5N diisobutylaluminum hydride/n-hexane solution was added to 10 ml of an anhydrous tetrahydrofuran solution containing 0.758 g of 2,5-diethoxycarbonylimidazo[5,1-b]thiazole, and the mixture was then stirred at -78° C. for 2 hours. Then, 10 ml of methanol was added to the reaction solution, and after stirring for 30 minutes, the solution was subjected to Celite filtration. The solvent was evaporated under reduced pressure, and the resulting crude product was purified by a silica gel column chromatograph to obtain 383.3 mg of the title compound.

Workup

  1. stirringafter stirring for 30 minutes
  2. filtrationthe solution was subjected to Celite filtration
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting crude product was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-25e6e4083a4143549ff8bfb5fd33c885
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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