Dichloromethane → HCID 86584238, compound

HRID 2288208Notes

Reaction equation

HRID 2288208 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7].[CH3:32][N:33]1[CH:37]=[C:36]([CH:38]=O)[CH:35]=[N:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:54]CCl>C(O)(=O)C>[ClH:54].[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:38][C:36]2[CH:35]=[N:34][N:33]([CH3:32])[CH:37]=2)[CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 54478438(2R)-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine

Product 1

HCID 86584238HCID 86584238, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To a mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine (0.2 g), 1-methyl-4-formyl-1H-pyrazole (50 mg), and sodium triacetoxyborohydride (151 mg) in dichloromethane (2 ml) was added one drop of acetic acid. After being stirred at room temperature overnight, the solution was evaporated under reduced pressure. The resulting residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate-methanol as eluent and treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[(1-methyl-1H-pyrazol-4-yl)methyl]piperazine hydrochloride (97 mg).

Workup

  1. customthe solution was evaporated under reduced pressure
  2. customThe resulting residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. additiontreated with 4N hydrogen chloride in ethyl acetate solution

Sources & evidence

ORD record
ord-33e19e6e951f4a7e80868bec4a63c350
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

Loading…