Water → HCID 46219099, compound

HRID 575938Notes

Reaction equation

HRID 575938 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-c9c95a4fda3740a191df070b64a814de
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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