Boron tribromide → HCID 21706300, compound

HRID 1594926Notes

Reaction equation

HRID 1594926 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([C:13]2([CH2:21][CH2:22][CH3:23])[O:18][CH2:17][CH2:16][N:15]([CH3:19])[C:14]2=[O:20])[CH:10]=[CH:11][CH:12]=1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[C:9]([C:13]2([CH2:21][CH2:22][CH3:23])[O:18][CH2:17][CH2:16][N:15]([CH3:19])[C:14]2=[O:20])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21706239HCID 21706239, compound

Product 1

HCID 21706300HCID 21706300, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (1M in CH2Cl2) (0.341 mL, 0.341 mmol) was added dropwise to a solution of 2-(-3-methoxy-phenyl)-4-methyl-2-propyl-morpholine-3-one, as described above in Step D, (0.06 g, 0.227 mmol) in CH2Cl2 (3 mL) at 0° C. with stirring. The ice bath was removed and stirring was continued for 16 h. The reaction mixture was quenched with H2O, concentrated to dryness, then dissolved in MeOH and purified by RP preparative HPLC on a PrepPak (95/5 to 5/95 H2O/CH3CN w/0.1% TFA, flow=65 mL/min) to give the title compound. FAB MS (M+1) 250.

Workup

  1. customThe ice bath was removed
  2. stirringstirring
  3. customThe reaction mixture was quenched with H2O
  4. concentrationconcentrated to dryness
  5. dissolutiondissolved in MeOH
  6. custompurified by RP preparative HPLC on a PrepPak (95/5 to 5/95 H2O/CH3CN w/0.1% TFA, flow=65 mL/min)

Sources & evidence

ORD record
ord-c7483fd9aa9a442db5f1101930823c65
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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