Pyridine, hydrofluoride (1:1) → HCID 53861240, compound

HRID 344063Notes

Reaction equation

HRID 344063 reaction equation
[O:1]1[C:3]2([CH2:19][O:20][C:21](=[O:35])[N:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:4][CH2:5][C:6]3[C:11]([CH:2]12)=[CH:10][CH:9]=[CH:8][C:7]=3[O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C1C=CN=CC=1.[FH:42]>C(Cl)Cl>[F:42][CH:2]1[C:11]2[C:6](=[C:7]([O:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1([OH:1])[CH2:19][O:20][C:21](=[O:35])[N:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 54053085HCID 54053085, compound

Product 1

HCID 53861240HCID 53861240, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,2-epoxy-2-(N,N-diphenylcarbamoyloxymethyl)-5-ethoxycarbonylmethyloxy-1,2,3,4-tetrahydronaphthalene (0.2 g) in CH2Cl2 (30 ml) was added HF-pyridine (0.5 ml) at 0° C. After being stirred for 2 hours, the solvent was removed in vacuo. The residue was extracted with ethyl acetate. The mixture was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-fluoro-2-hydroxy-2-(N,N-diphenylcarbamoyloxymethyl)-5-ethoxycarbonylmethyloxy-1,2,3,4-tetrahydronaphthalene (70 mg)

Workup

  1. customthe solvent was removed in vacuo
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe mixture was washed with 1N-HCl solution, sat. NaHCO3, and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-bd50f14a0685424188218f02d3b0a375
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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