Potassium Carbonate → HCID 25145780, compound

HRID 1931819Notes

Reaction equation

HRID 1931819 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:22][CH2:23][CH3:24]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH2:22][CH2:23][CH3:24])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 63585886HCID 63585886, compound

Product 1

HCID 25145780HCID 25145780, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 24: Enantiomer E1 of 3-(3,5-difluorophenyl)-pyrrolidin-3-ol (0.53 g, 2.66 mmol), acetonitrile (3 mL), potassium carbonate (0.55 g, 3.99 mmol) and iodopropane (260 μl, 2.66 mmol). Purification by HPLC on Waters OBD 018, 5 μm (MeOH/33 mM NH3, 40:60 to 60:40). Yield: 0.274 g. [α]D=+21.2° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diethyl ether: M.p. 117-118° C.; MS m/z (relative intensity, 70 eV) 241 (M+, 8), 212, (bp), 182 (35), 127 (12), 84 (45).

Workup

  1. customPreparation
  2. customPurification by HPLC on Waters OBD 018, 5 μm (MeOH/33 mM NH3, 40:60 to 60:40)
  3. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-df57618852564cd68c484dc725b6891b
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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