Boron tribromide → HCID 67436986, compound
Reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:16]C)=[CH:9][CH:10]=3)[C@@:5]3([N:22]=[C:21]([NH2:23])[CH2:20][O:19][CH2:18]3)[C:4]=2[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:23][C:21]1[CH2:20][O:19][CH2:18][C@@:5]2([C:4]3[CH:3]=[C:2]([Br:1])[CH:15]=[CH:14][C:13]=3[O:12][C:11]3[C:6]2=[CH:7][C:8]([OH:16])=[CH:9][CH:10]=3)[N:22]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 250-mL flask, the (R)-2′-bromo-7′-methoxy-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-5-amine (0.393 g, 1.047 mmol) was dissolved in dcm (10 mL). The solution was cooled to 0° C. A DCM solution of boron tribromide (1.0 M, 3.14 mL, 3.14 mmol) was added. After 1.5 h, the mixture was quenched with 9:1 saturated aqueous NH4Cl/NH4OH (10 mL). The mixture was diluted further with water (10 mL) and the aqueous phase was extracted with 5% MeO/DCM (3×50 mL). The organics were combined, washed with dilute brine (10 mL), dried over sodium sulfate and concentrated to afford crude (R)-5-amino-2′-bromo-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-7′-ol (349 mg, 0.966 mmol), which was used directly in the next step.
Workup
- customthe mixture was quenched with 9:1 saturated aqueous NH4Cl/NH4OH (10 mL)
- additionThe mixture was diluted further with water (10 mL)
- extractionthe aqueous phase was extracted with 5% MeO/DCM (3×50 mL)
- washwashed with dilute brine (10 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1eeab0b323024002bd3d545f71176e58
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497264B2
Reaction notes
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