Iodoethane → HCID 25102809, compound

HRID 1931794Notes

Reaction equation

HRID 1931794 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-].[Na+].[Na+].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 10340Sodium CarbonateHCID 63585886HCID 63585886, compound

Product 1

HCID 25102809HCID 25102809, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a sealed tube a mixture of enantiomer E2 of 3-(3,5-difluorophenyl)pyrrolidin-3-ol (0.17 g, 0.85 mmol), acetonitrile (4 mL), sodium carbonate (0.11 g, 2.12 mmol) and iodoethane (0.13 g, 0.85 mmol) was stirred at ambient temperature for 72 h. Water (30 mL) was added and the aqueous phase was 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, 1:1) gave the title compound (0.11 g). [α]D=−21.4° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diisopropyl ether: M.p. 111-112° C.; MS m/z (relative intensity, 70 eV) 227 (M+, 19), 212 (15), 141 (15), 127 (15), 71 (bp).

Workup

  1. extractionthe aqueous phase was 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, 1:1)

Sources & evidence

ORD record
ord-e2cae662b8844b3fb9226db994034a84
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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