2,3-Difluorophenol → HCID 44313262, compound

HRID 2259200Notes

Reaction equation

HRID 2259200 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])=O)(C)(C)C.[F:15][C:16]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=1O>C1COCC1>[F:15][C:16]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=1[O:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1

Participants

4

Reactant 2

HCID 808792,3-DifluorophenolHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 44313262HCID 44313262, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 4.03 g (20 mmol) sample of (S)-1-t-butoxycarbonyl-2-pyrrolidinemethanol (from Example 3a above) and 3.90 g (30 mmol) of 2,3-difluorophenol (Aldrich) were added to a complex of TPP and TBAD, (prepared as in Example 5b above, 30 mmol of each) in 150 mL of THF. The reaction was stirred for 40 hr, and the solvents were removed under vacuum. Hexane was added to the residue, and the crude product was collected by filtration. The product was washed with hexane and 10% NaOH, then purified by flash chromatography on silica gel, eluting with CHCl3. Removal of the solvent gave 7.5 g of the title compound.

Workup

  1. customthe solvents were removed under vacuum
  2. additionHexane was added to the residue
  3. filtrationthe crude product was collected by filtration
  4. washThe product was washed with hexane and 10% NaOH
  5. custompurified by flash chromatography on silica gel
  6. washeluting with CHCl3
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-6abfc2e79def4ccda9d6d851d9cc8155
Source dataset
uspto-grants-1995_12
Patent number
US05472958

Reaction notes

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