Sodium Iodide → HCID 53803408, compound

HRID 2400022Notes

Reaction equation

HRID 2400022 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[OH:9][CH2:10][C@@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1.Br[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28]([O:30][CH3:31])=[O:29]>C(#N)C.ClCCl>[OH:9][CH2:10][C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28]([O:30][CH3:31])=[O:29]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 640091L-ProlinolHCID 10589341HCID 10589341, compound

Product 1

HCID 53803408HCID 53803408, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

0.92 g of potassium carbonate, 0.22 g of sodium iodide and then 0.63 g of 2-hydroxymethyl-(S)-pyrrolidine are successively added to a solution of 1.8 g of methyl 2-(3-bromopropoxy)phenylacetate in 20 cm3 of acetonitrile. The reaction mixture is heated at 70° C. for 5 hours and then, after cooling, diluted with 100 cm3 of dichloromethane, washed with 100 cm3 of water and then with 100 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 3 cm, height 30 cm), eluting under a nitrogen pressure of 0.4 bar with an ethyl acetate and methanol mixture (90/10 by volume) and collecting fractions of 100 cm3. Fractions 7 to 20 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). 1.55 g of methyl 2-[3-(2-hydroxymethyl-(S)-1-pyrrolidinyl)propoxy]-phenylacetate are obtained in the form of an oil.

Workup

  1. temperatureafter cooling
  2. washwashed with 100 cm3 of water
  3. dry with materialwith 100 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 3 cm, height 30 cm)
  6. washeluting under a nitrogen pressure of 0.4 bar with an ethyl acetate and methanol mixture (90/10 by volume)
  7. customcollecting fractions of 100 cm3
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-831d5667402147e4a1d2c81687c2850f
Source dataset
uspto-grants-1995_09
Patent number
US05451601

Reaction notes

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