Ethanol → HCID 11749254, compound

HRID 964520Notes

Reaction equation

HRID 964520 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OC)[C:5]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])(OC)[CH:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[CH2:27]([OH:29])C.O1CCC[CH2:31]1.[BH4-].[Na+].[OH2:37]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:6]([CH:15]=1)[CH:7]([OH:8])[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([O:37][CH3:31])[C:14]=1[O:29][CH3:27]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 19077169HCID 19077169, compound

Product 1

HCID 11749254HCID 11749254, compoundYield 90%

Conditions

Temperature
40 °C

Procedure

To 100 mg of 5-chloro-2-pivaloylamino-2,3-dimethoxybenzophenone were added 2 ml of ethanol and 0.1 ml of tetrahydrofuran and the mixture was warmed to about 40° C. for dissolution. After the solution was cooled to 25° C., 29 mg of sodium borohydride was added and the reaction was carried out with stirring at 25°-33° C. for 5 hours. The reaction mixture was diluted with 0.1 ml of water and distilled under reduced pressure. The residue was dissolved in 1 mL of methylene chloride and the solution was washed with 1 L of water and distilled under reduced pressure. The residue was dissolved in 0.2 L of methylene chloride followed by addition of 2 mL of n-hexane, whereupon white crystals separated out. The crystals were harvested by filtration, washed with 0.5 mL of n-hexane, and dried under reduced pressure to provide 90.4 mg of 5-chloro-2-pivaloylamino-α-(2',3'-dimethoxyphenyl)benzyl alcohol. Yield 90%.

Workup

  1. temperatureAfter the solution was cooled to 25° C.
  2. distillationdistilled under reduced pressure
  3. dissolutionThe residue was dissolved in 1 mL of methylene chloride
  4. washthe solution was washed with 1 L of water
  5. distillationdistilled under reduced pressure
  6. dissolutionThe residue was dissolved in 0.2 L of methylene chloride
  7. additionfollowed by addition of 2 mL of n-hexane, whereupon white crystals
  8. customseparated out
  9. filtrationThe crystals were harvested by filtration
  10. washwashed with 0.5 mL of n-hexane
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-32d6a33fbcf043988a666cb978a6880d
Source dataset
uspto-grants-1998_06
Patent number
US05770438

Reaction notes

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