Water → HCID 131724988, compound

HRID 1071400Notes

Reaction equation

HRID 1071400 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][O:7][CH2:8][C@H:9]1[NH:14][C:13](=[O:15])[CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:10]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.I[CH3:39].[H-].[Na+].O>C1COCC1>[F:35][C:32]([F:33])([F:34])[C:30]1[CH:29]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:36])[F:37])[CH:31]=1)[CH2:6][O:7][CH2:8][C@H:9]1[N:14]([CH3:39])[C:13](=[O:15])[CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:10]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131724989HCID 131724989, compound

Product 1

HCID 131724988HCID 131724988, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (2S,3S)-3-(3,5-bis(trifluoromethyl)benzyloxymethyl)-5-oxo-2-phenylpiperizine-1-carboxylate (6.6 g, 12.4 mmol) and iodomethane (1.0 mL, 16.1 mmol) in THF (50 mL) was added NaH (0.55 g, 13.6 mmol) at 0° C. After stirring overnight, the reaction was stopped with water (50 mL). The product was extracted with ether, and purified by washing with 0.5 mol/L KHSO4 solution, saturated NaHCO3 solution and saturated brine in order. The organic layer was dried over sodium sulfate anhydride. Sodium sulfate was filtered off and the solvent was removed by evaporation from the filtrate under reduced pressure to give tert-Butyl (2S,3S)-3-(3,5-bis(trifluoromethyl)benzyloxymethyl)-4-methyl-5-oxo-2-phenylpiperizine-1-carboxylate 6.5 g (96%) was obtained.

Workup

  1. extractionThe product was extracted with ether
  2. custompurified
  3. washby washing with 0.5 mol/L KHSO4 solution, saturated NaHCO3 solution and saturated brine in order
  4. dry with materialThe organic layer was dried over sodium sulfate anhydride
  5. filtrationSodium sulfate was filtered off
  6. customthe solvent was removed by evaporation from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-8fc4535f311a4944ae926f657f413669
Source dataset
uspto-grants-2005_06
Patent number
US06906074B2

Reaction notes

Loading…