Iodoethane → HCID 25102809, compound

HRID 1931795Notes

Reaction equation

HRID 1931795 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:15](#N)[CH3:16].C(=O)([O-])[O-].[K+].[K+].ICC>O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH2:15][CH3:16])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 63585886HCID 63585886, compound

Product 1

HCID 25102809HCID 25102809, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

In a sealed tube a mixture of enantiomer E1 of 3-(3,5-difluorophenyl)pyrrolidin-3-ol (0.14 g, 0.70 mmol), acetonitrile (4 mL), potassium carbonate (0.09 g, 1.75 mmol) and iodoethane (0.12 g, 0.77 mmol) was heated under microwave irradiation at 100° C. for 5 minutes. Water (30 mL) was added and the aqueous phase extracted with ethyl acetate (2×50 mL), the combined organic phase was dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 2:1 to 1:1) gave the title compound (0.11 g). [α]D=+18.7° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diisopropyl ether: M.p. 137-139° C.; MS m/z (relative intensity, 70 eV) 227 (M+, 19), 212 (15), 141 (15), 127 (15), 71 (bp).

Workup

  1. extractionthe aqueous phase extracted with ethyl acetate (2×50 mL)
  2. dry with materialthe combined organic phase was dried (MgSO4)
  3. customevaporated
  4. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 2:1 to 1:1)

Sources & evidence

ORD record
ord-5d6b4539a5fa44de8f52ef43cd53e2e0
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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