Boron tribromide → HCID 21714267, compound

HRID 1600640Notes

Reaction equation

[Cl:1][C:2]1[C:10]([O:11]C)=[CH:9][C:8]2[C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH2:17][N:6]3[C:7]=2[C:3]=1[CH:4]=[C:5]3[C:19]([O:21][CH2:22][CH3:23])=[O:20].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]2[C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH2:17][N:6]3[C:7]=2[C:3]=1[CH:4]=[C:5]3[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of ethyl 5,6,7,8-tetrahydro-11-chloro-10-methoxy-8-oxo-4H-azocino[3,2,1-hi]indole-2-carboxylate (4.00 g, 11.8 mmol) in dichloromethane (80 ml) was cooled to -78° C., and boron tribromide (3.26 g, 13.0 mmol) was added dropwise. The reaction temperature was raised to -20° C. and the reaction mixture was stirred at -20° C. for 8 hours. The reaction mixture was poured into ice water and extracted three times with ethylacetate, and the extract solution was washed with a saturated aqueous ammonium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9) to obtain 0.99 g of ethyl 5,6,7,8-tetrahydro-11-chloro-10-hydroxy-8-oxo-4H-azocino[3,2,1-hi]indole-2-carboxylate.

Workup

extractionextracted three times with ethylacetate
washthe extract solution was washed with a saturated aqueous ammonium chloride solution
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record: ord-765bf56e232a4444bae08711d75c544b
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977100

Reaction notes

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