Boron trifluoride etherate → HCID 67834999, compound

HRID 1460494Notes

Reaction equation

HRID 1460494 reaction equation
B(F)(F)F.CCOCC.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][S:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26]([C@@H:28]1[CH2:32][CH2:31][CH2:30][N:29]1[C:33](=O)[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)=O.[BH4-].[Na+]>O1CCCC1>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][S:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][CH2:26][C@@H:28]1[CH2:32][CH2:31][CH2:30][N:29]1[CH2:33][CH2:34][C:35]1[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 67834914HCID 67834914, compound

Product 1

HCID 67834999HCID 67834999, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boron trifluoride etherate (1531 g, 1327 ml) was added over ten minutes to a stirred, ice-cooled solution of (2S)-(N-[2-(2-bromophenylmethylthio)phenyl])carbamoyl-1-(4-methoxyphenylacetyl)pyrrolidine (see Preparation 23) (1750 g) and sodium borohydride (306.2 g) in tetrahydrofuran (8.73 L). The mixture was stirred at room temperature for one hour, heated under reflux for two hours, cooled, evaporated under reduced pressure to reduced volume to remove the tetrahydrofuran, quenched by the cautious addition of water and further evaporated under reduced pressure. The residue was treated with 40% aqueous sodium hydroxide solution (5 L) and the mixture was heated under reflux for two hours, cooled to room temperature by the addition of ice, acidified to pH 6-7 with concentrated hydrochloric acid and extracted with dichloromethane. The combined organic extracts were washed with 1M aqueous sodium hydroxide solution followed by water, dried over magnesium sulphate and evaporated under reduced pressure to give the desired compound (1589 g, 96%) as a brown oil which was characterised by 1H-NMR spectroscopy.

Workup

  1. temperatureheated
  2. temperatureunder reflux for two hours
  3. temperaturecooled
  4. customevaporated under reduced pressure to reduced volume
  5. customto remove the tetrahydrofuran
  6. customquenched by the cautious addition of water
  7. customfurther evaporated under reduced pressure
  8. additionThe residue was treated with 40% aqueous sodium hydroxide solution (5 L)
  9. temperaturethe mixture was heated
  10. temperatureunder reflux for two hours
  11. temperaturecooled to room temperature by the addition of ice
  12. extractionextracted with dichloromethane
  13. washThe combined organic extracts were washed with 1M aqueous sodium hydroxide solution
  14. dry with materialdried over magnesium sulphate
  15. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5637675c07544285ae7ac112d5ee4a2e
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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