Water → HCID 59511560, compound

HRID 1158516Notes

Reaction equation

HRID 1158516 reaction equation
C(O[N:9]=[C:10]1[C:17]2[CH:16]=[CH:15][S:14][C:13]=2[CH2:12][CH:11]1[OH:18])C1C=CC=CC=1.B.O.[OH-].[K+]>C1COCC1.[Cl-].[Na+].O>[NH2:9][C@@H:10]1[C:17]2[CH:16]=[CH:15][S:14][C:13]=2[CH2:12][C@@H:11]1[OH:18]

Participants

7

Reactant 4

HCID 962WaterHCID 6331BoraneHCID 14797Potassium HydroxideHCID 72311086HCID 72311086, compound

Product 1

HCID 59511560HCID 59511560, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 5-hydroxy-5,6-dihydro-cyclopenta[b]thiophen-4-one O-benzyl-oxime (55.1 g, 0.212 mol) was added drop wise at about 5° C. to 1.0 M solution of borane in THF (650 mL) and the mixture was stirred at room temperature overnight. The mixture was refluxed for two hours and cooled to about 5° C. Water (70 mL) and 20% potassium hydroxide solution (80 mL) was added dropwise. The mixture was refluxed for two hours and cooled. Brine was added and the THF removed under reduced pressure. The mixture was extracted five times with DCM, dried with sodium sulphate and evaporated under reduced pressure. The product was purified by silica gel chromatography with DCM and 10% methanol. Yield: 17.8 g=54%

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. temperaturecooled to about 5° C
  3. temperatureThe mixture was refluxed for two hours
  4. temperaturecooled
  5. customthe THF removed under reduced pressure
  6. extractionThe mixture was extracted five times with DCM
  7. dry with materialdried with sodium sulphate
  8. customevaporated under reduced pressure
  9. customThe product was purified by silica gel chromatography with DCM and 10% methanol

Sources & evidence

ORD record
ord-485a7b2f2b54485b8a29663654c440e8
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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