Water → HCID 68291729, compound

HRID 2404596Notes

Reaction equation

HRID 2404596 reaction equation
O.C[Si]([Cl:6])(C)C.[CH3:7][N:8]([CH2:10][CH:11]1[CH2:17][CH2:16][CH:15]2[CH:13]([CH2:14]2)[C:12]1([C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[C:21]([F:26])[CH:20]=1)[OH:18])[CH3:9]>CC(=O)CC>[ClH:6].[CH3:9][N:8]([CH2:10][CH:11]1[CH2:17][CH2:16][CH:15]2[CH:13]([CH2:14]2)[C:12]1([C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[C:21]([F:26])[CH:20]=1)[OH:18])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 60152194HCID 60152194, compound

Product 1

HCID 68291729HCID 68291729, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Add H2O (18 mg, 1.0 mmol) and TMSCl (92 mg, 0.857 mmol) to a solution of 3-dimethylaminomethyl-2-(3-fluoro-5-hydroxy-phenyl)-bicyclo[4.1.0]heptan-2-ol (218 mg, 0.781 mmol) in 2-butanone (70 mL). Then stir the reaction mixture at room temperature for 2 hours. After removal the solvent by evaporation, wash the residue with EtOAc (3 mL×2) to give 3-dimethylaminomethyl-2-(3-fluoro-5-hydroxy-phenyl)-bicyclo[4.1.0]heptan-2-ol hydrochloride as white solid (72 mg, Yield: 67.8%). 1H NMR (400 MHz, D2O) δ 6.93 (s, 1H), 6.87-6.89 (d, J=9.6, 1H), 6.42-6.58 (m, 1H), 3.32-3.33 (t, J=3.2, 1H), 2.98-3.04 (m, 1H), 2.77 (m, 6H), 2.22-2.23 (m, 1H), 2.06 (m, 1H), 1.81-1.85 (m, 2H), 1.61-1.71 (m, 1H), 1.17-1.21 (m, 1H), 1.08-1.10 (m, 1H), 0.83-0.86 (m, 1H), 0.56-0.60 (m, 1H).

Workup

  1. customAfter removal the solvent
  2. customby evaporation
  3. washwash the residue with EtOAc (3 mL×2)

Sources & evidence

ORD record
ord-896e5952e8f445c59983ba2cd541c4c4
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

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