Boron tribromide → HCID 11226424, compound

HRID 1374987Notes

Reaction equation

HRID 1374987 reaction equation
B(Br)(Br)Br.[CH2:5]([N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:33])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)[C@H:14]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[C:37]([O:42]C)[CH:36]=2)[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH2:5]([N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:33])[C:19]2[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)[C@H:14]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[C:37]([OH:42])[CH:36]=2)[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 12016231HCID 12016231, compound

Product 1

HCID 11226424HCID 11226424, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide in dichloromethane (1M solution, 3.7 ml) was added dropwise over 20 minutes to an ice-cooled solution of (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3-methoxy-4-methylbenzyl)-piperazine (0.68 g) in dichloromethane (5 ml). After being stirred at the same temperature for 2 hours, followed by further stirring at room temperature for 12 hours, the mixture was poured into aqueous saturated 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 mixed solvents of hexane and ethyl acetate (4:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3-hydroxy-4-methylbenzyl)piperazine (0.56 g) as a red foam.

Workup

  1. stirringby further stirring at room temperature for 12 hours
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additionmixed solvents of hexane and ethyl acetate (4:1)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c03f41a21d1c419cb5ed7f7aeb24aef8
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

Loading…