Hydrogen Peroxide → HCID 10076974, compound

HRID 496031Notes

Reaction equation

HRID 496031 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:34])[C:22]3[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=3)[CH2:17][CH2:16]2)=[O:14])=[CH:4][CH:3]=1.[BH4-].[Na+].B(F)(F)F.CC[O:50]CC.[OH-].[Na+].OO>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)[CH:9]([OH:50])[CH2:10][CH2:11][CH2:12][C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:34])[C:22]3[CH:23]=[C:24]([O:32][CH3:33])[C:25]([O:30][CH3:31])=[C:26]([O:28][CH3:29])[CH:27]=3)[CH2:17][CH2:16]2)=[O:14])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride2×HCID 10460533HCID 10460533, compound

Product 1

HCID 10076974HCID 10076974, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6,6-bis-(4-fluoro-phenyl)-1-[4-(3,4,5,-trimethoxy-benzoyl)-piperazin-1-yl]-hex-5-en-1-one (1.3 g, 2.3 mmol) in dry THF (20 ml) was added NaBH4 (22 mg, 0.58 mmol) followed by dropwise addition of BF3.Et2O (0.2 ml, 1.43 mmol). The resulting mixture stirred at r.t. for 3 hrs and excess NaBH4 decomposed by addition of water(0.1 ml). The mixture was then oxidized by adding 3M NaOH (0.3 ml) followed by addition of H2O2 (0.5 ml, 3 mmol). After stirring for 1.5 hrs at 30-40° C., the mixture was washed with brine (30 ml). The organic layer dried over MgSO4 and evaporated. The residue was purified by column chromatography using EtOAc:hexane (3:1) to give the desired product in 64% yield.

Workup

  1. stirringAfter stirring for 1.5 hrs at 30-40° C.
  2. washthe mixture was washed with brine (30 ml)
  3. dry with materialThe organic layer dried over MgSO4
  4. customevaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d85b4840b5fa4a6596f77ca9d0413e95
Source dataset
uspto-grants-2005_09
Patent number
US06943168B2

Reaction notes

Loading…