Boron tribromide → HCID 54529854, compound

HRID 2416710Notes

Reaction equation

HRID 2416710 reaction equation
C[O:2][C:3]1[CH:27]=[CH:26][C:6]2[CH2:7][C@@H:8]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:9](=[O:20])[N:10]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][C:5]=2[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:27]=[CH:26][C:6]2[CH2:7][C@@H:8]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:9](=[O:20])[N:10]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 54237374HCID 54237374, compound

Product 1

HCID 54529854HCID 54529854, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (S)-8-methoxy-3-oxo-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (2.61 g, 7.1 mmole) in CH2Cl2 (40 mL) was added BBr3 (21.3 mL, 1M in CH2Cl2, 21.3 mmole) at −20° C. After 45 minutes the mixture was quenched with MeOH (200 mL) and concentrated. The residue was filtered through a silica gel plug using 50% EtOAc/hexanes as eluent. The resulting orange solid was recrystallized from MeOH/H2O to give the title compound as an off-white solid (2.16 g, 81%): MS (ES) m/e 376 (M+Na)+.

Workup

  1. customAfter 45 minutes the mixture was quenched with MeOH (200 mL)
  2. concentrationconcentrated
  3. filtrationThe residue was filtered through a silica gel plug
  4. customThe resulting orange solid was recrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-0a469f3b85e34fa19287232d6cd19f89
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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