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

HRID 963733Notes

Reaction equation

HRID 963733 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
  4. dry with materialHCl solution, sat. NaHCO3, and brine, dried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-0dd600d6da3642e3b1c904587c05f981
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

Loading…