Borane;tetrahydrofuran → F15845

HRID 601734Notes

Reaction equation

HRID 601734 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][CH2:4][C@H:3]([NH:12][C:13](=O)[C@H:14]([CH3:25])[CH2:15][S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:2]1.B.C1COCC1>C1COCC1>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[S:16][CH2:15][C@@H:14]([CH3:25])[CH2:13][NH:12][C@H:3]1[CH2:4][S:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:1][CH2:2]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 16115314HCID 16115314, compound

Product 1

HCID 11566989F15845Yield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a round-bottom flask maintained under an inert atmosphere, 250 mg (0.642 mmole) of (2S)-N-[(3R)-3,4-dihydro-2H-1,5-benzoxathiepin-3-yl]-3-[(2-methoxyphenyl)sulfanyl]-2-methylpropanamide (9a-1) and 7.5 mL of anhydrous THF are introduced. Next, 3.21 mL (3.21 mmoles) of 1 M BH3.THF is added dropwise, then the solution is heated to reflux for 1 h 30 min. The mixture is cooled, concentrated under reduced pressure, taken up with 20 mL of methanol, then acidified with 36% hydrochloric acid. The mixture is brought to reflux for 4 hours then stirred for 12 hours at ambient temperature. The reaction mixture is concentrated under reduced pressure then made basic (pH=10) by adding concentrated soda. The aqueous phase is extracted with dichloromethane, the combined organic phases are washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The title compound is obtained in the form of a colorless oil (232 mg, 0.618 mmole).

Workup

  1. additionare introduced
  2. temperaturethe solution is heated
  3. temperatureto reflux for 1 h 30 min
  4. temperatureThe mixture is cooled
  5. concentrationconcentrated under reduced pressure
  6. temperatureto reflux for 4 hours
  7. concentrationThe reaction mixture is concentrated under reduced pressure
  8. additionby adding
  9. concentrationconcentrated soda
  10. extractionThe aqueous phase is extracted with dichloromethane
  11. washthe combined organic phases are washed with brine
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-71d5ffc0a07e40f48bb2a87a651afc37
Source dataset
uspto-grants-2011_03
Patent number
US07902381B2

Reaction notes

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