Borane → HCID 57554531, compound

HRID 551937Notes

Reaction equation

HRID 551937 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]3[C:19](=[O:20])[O:18][C:17]([CH3:22])([CH3:21])[O:16][C:15]=3[CH:23]=2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.B>C1COCC1>[CH:1]1([CH2:6][CH2:7][CH2:8][NH:10][C:11]2[CH:12]=[CH:13][C:14]3[C:19](=[O:20])[O:18][C:17]([CH3:21])([CH3:22])[O:16][C:15]=3[CH:23]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6331Borane2×HCID 575545043-cyclopentyl-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)propanamide

Product 1

HCID 57554531HCID 57554531, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 3-cyclopentyl-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)propanamide (2.57 g, 8.08 mmol) in THF (30 mL) was added a solution of borane in THF (24.3 ml, 24.3 mmol, 1M) and the resulting mixture was stirred at rt for 2 hrs. The mixture was then refluxed for 2 hrs. A solution of borane in THF (10.0 ml, 10.0 mmol, 1M) was added again and the mixture was refluxed for an additional 5 hrs. The reaction was quenched with HCl 5 N. Then the solution was made basic by the addition of an aqueous solution of NaOH (5N) and extracted with Et2O (3×). The combined organic layers were dried over MgSO4 and the solvents were removed under reduced pressure. Purification by flash chromatography on silicagel (EtOAc/c-Hex (20/80)) gave 2.1 g (86%) of the title compound as a white solid.

Workup

  1. temperatureThe mixture was then refluxed for 2 hrs
  2. temperaturethe mixture was refluxed for an additional 5 hrs
  3. customThe reaction was quenched with HCl 5 N
  4. additionThen the solution was made basic by the addition of an aqueous solution of NaOH (5N)
  5. extractionextracted with Et2O (3×)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customthe solvents were removed under reduced pressure
  8. customPurification by flash chromatography on silicagel (EtOAc/c-Hex (20/80))

Sources & evidence

ORD record
ord-3b217de0b50647af9fb38698402955a2
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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