Boron tribromide → HCID 90449646, compound
Reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17]C)[CH:15]=3)[N:10]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[N:10]([C:19](=[O:24])[C:20]([F:22])([F:23])[F:21])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
1-(1′-Acetyl-5-methoxyspiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (2.74 g, 8.00 mmol) was dissolved in methylene chloride (50 mL). Thereafter, 1 M boron tribromide (40 mL, 40.0 mmol) was added to the above obtained solution at −78° C., and the thus obtained mixture was then stirred at −20° C. for 3 hours. Thereafter, the reaction solution was poured into ice water, and was then extracted with chloroform. The organic layer was washed with water and brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to obtain 1-(1′-acetyl-5-hydroxyspiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (2.39 g, 91%) in the form of a dark brown solid.
Workup
- extractionwas then extracted with chloroform
- washThe organic layer was washed with water and brine
- dry with materialwas then dried over anhydrous sodium sulfate
- concentrationfollowed by concentration in vacuo
- customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
Sources & evidence
- ORD record
- ord-262beddee4ac4c0f8ded3adb2f660e13
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921576B2
Reaction notes
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