Water → HCID 46219099, compound

HRID 1188151Notes

Reaction equation

HRID 1188151 reaction equation
[Cl:1][C:2]1[C:3]([F:15])=[C:4]([C:8]2([O:13][CH3:14])[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:16](N(CC)CC)[CH3:17].ICC.O>O1CCCC1>[Cl:1][C:2]1[C:3]([F:15])=[C:4]([C:8]2([O:13][CH3:14])[CH2:12][CH2:11][N:10]([CH2:16][CH3:17])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 8471TriethylamineHCID 46196348HCID 46196348, compound

Product 1

HCID 46219099HCID 46219099, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (+)-3-(3-chloro-2-fluorophenyl)-3-methoxypyrrolidine (0.25 g, 1.08 mmol) and triethylamine (0.305 ml, 2.17 mmol) in tetrahydrofuran (20 ml), was added iodoethane (0.13 ml, 1.63 mmol) and the solution was stirred at ambient temperature for 26 h. Water (20 ml) was added and the aqueous phase was extracted with EtOAc (2×50 ml), the combined organic phase was dried (Na2SO4) and the solvent was evaporated. Purification by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 65:35) gave the title compound 0.106 g (38%). [a]D=+16.5° (methanol). The amine was converted to the fumaric acid salt and recrystallized from 2-propanol/diisopropyl ether: M.p. 131-133° C. MS m/z (rel. intensity, 70 eV) 257 (M+, 9), 242 (bp), 227 (44), 157 (44), 71 (89).

Workup

  1. extractionthe aqueous phase was extracted with EtOAc (2×50 ml)
  2. dry with materialthe combined organic phase was dried (Na2SO4)
  3. customthe solvent was evaporated
  4. customPurification by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 65:35)

Sources & evidence

ORD record
ord-7a531039f9214aa9a1a8cfcc8db12719
Source dataset
uspto-grants-2014_03
Patent number
US08673962B2

Reaction notes

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