Water → 2-Dimethylaminomethyl-3-(2-fluoro-5-hydroxy-phenyl)-bicyclo[3.2.1]octan-3-ol hydrochloride

HRID 2404584Notes

Reaction equation

HRID 2404584 reaction equation
O.C[Si]([Cl:6])(C)C.[CH3:7][N:8]([CH2:10][CH:11]1[C:17]([C:19]2[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:20]=2[F:26])([OH:18])[CH2:16][CH:15]2[CH2:27][CH:12]1[CH2:13][CH2:14]2)[CH3:9]>CC(=O)CC>[ClH:6].[CH3:9][N:8]([CH2:10][CH:11]1[C:17]([C:19]2[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:20]=2[F:26])([OH:18])[CH2:16][CH:15]2[CH2:27][CH:12]1[CH2:13][CH2:14]2)[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 601524522-Dimethylaminomethyl-3-(2-fluoro-5-hydroxy-phenyl)-bicyclo[3.2.1]octan-3-ol

Product 1

HCID 682915872-Dimethylaminomethyl-3-(2-fluoro-5-hydroxy-phenyl)-bicyclo[3.2.1]octan-3-ol hydrochlorideYield 83.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Add H2O (175.1 mg, 9.73 mmol) and TMSCl (1.057 g, 9.73 mmol) to a solution of 2-dimethylaminomethyl-3-(2-fluoro-5-hydroxy-phenyl)-bicyclo[3.2.1]octan-3-ol (2.38 g, 8.11 mmol) in 2-butanone (60 mL). Stir the reaction mixture at ambient temperature for 3 hours. After removal solvent by evaporation, wash the residue with EtOAc to give 2-dimethylaminomethyl-3-(2-fluoro-5-hydroxy-phenyl)-bicyclo[3.2.1]octan-3-ol hydrochloride as white solid (2.23 g, Yield: 83.5%). 1H NMR (400 MHz, D2O) δ 6.89-6.93 (m, 2H), 6.66-6.70 (m, 1H), 3.10-3.14 (m, 1H), 2.59-2.65 (m, 4H), 2.42-2.44 (d, J=8.0, 1H), 2.36-2.41 (d, J=20.0, 3H), 2.30-2.33 (d, J=12.0, 2H), 2.18 (s, 1H), 1.89-1.95 (m, 1H), 1.74-1.78 (m, 1H), 1.51-1.67 (m, 4H), 1.47-1.50 (m, 1H).

Workup

  1. customAfter removal solvent
  2. customby evaporation
  3. washwash the residue with EtOAc

Sources & evidence

ORD record
ord-44acc82f2f43463eb831a22e044b1358
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

Loading…