Boron tribromide → 4-(3-Fluoro-4-hydroxy-phenyl)-1-methanesulfonyl-piperidin-4-ol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:11][CH2:12][N:13]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.B(Br)(Br)Br.C(=O)(O)[O-:25].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:10]2([OH:25])[CH2:11][CH2:12][N:13]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:14][CH2:15]2)[CH:5]=[CH:6][C:7]=1[OH:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
4-(3-Fluoro-4-methoxy-phenyl)-1-methanesulfonyl-1,2,3,6-tetrahydro-pyridine (1.12 g, 3.93 mmol) is dissolved in dry dichloromethane (20 mL) under nitrogen. The solution is cooled to −78° C. and boron tribromide (11.52 g, 7.85 mL, 7.85 mmol) is added by syringe. The reaction is warmed to room temperature and stirred for 1 h followed by the addition of 5% aqueous sodium bicarbonate and dichloromethane. An insoluble solid is formed and filtered to provide 729 mg of the title compound as a pink solid. 1H NMR (CDCl3) δ (ppm): 7.21 (dd, 1H), 7.09 (m, 1H), 6.89 (t, 1H), 3.30 (m, 2H), 3.18 (td, 2H), 2.88 (m, 3H), 2.06 (m, 2H), 1.80 (m, 2H).
Workup
- temperatureThe reaction is warmed to room temperature
- customAn insoluble solid is formed
- filtrationfiltered
Sources & evidence
- ORD record
- ord-0322eb58906b455fa23a44e35dc654fb
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207344B2
Reaction notes
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