1,1'-Difluoro-2,2'-bipyridinium Bis(tetrafluoroborate) → HCID 68503284, compound

HRID 1712620Notes

Reaction equation

HRID 1712620 reaction equation
[OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:3]1.[F:25][B-](F)(F)F.F[B-](F)(F)F.F[N+]1C=CC=CC=1C1C=CC=C[N+]=1F.[Na]>C(#N)C>[F:25][C:12]1[CH:13]=[C:8]([CH:7]2[CH2:6][CH2:5][N:4]([C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])[CH2:3][CH:2]2[OH:1])[CH:9]=[CH:10][C:11]=1[OH:14]

Participants

5

Reactant 3

HCID 27339311,1'-Difluoro-2,2'-bipyridinium Bis(tetrafluoroborate)HCID 5360545SodiumHCID 68500730Benzyl 3-hydroxy-4-(4-hydroxyphenyl)piperidinecarboxylate

Product 1

HCID 68503284HCID 68503284, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.581 g of benzyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate in 5 ml of acetonitrile is admixed with 0.320 g of N,N′-difluoro-2,2′-bipyridinium bis(tetrafluoroborate) and the suspension is subsequently heated at reflux over 15 hours. The reaction mixture is poured onto 10 ml of saturated aqueous sodium thiosulpphate solution and the mixture is extracted with 2×50 ml of ethyl acetate. The combined organic phases are washed with 10 ml each of 0.5 M HCl and brine, dried over sodium sulphate and concentrated. The title compound is obtained as a colourless solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.33 (2:1 EtOAc-heptane); Rt=3.80.

Workup

  1. temperaturethe suspension is subsequently heated
  2. temperatureat reflux over 15 hours
  3. extractionthe mixture is extracted with 2×50 ml of ethyl acetate
  4. washThe combined organic phases are washed with 10 ml each of 0.5 M HCl and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e3eeb96eb8e94c45ab51d9c9b94f4e9a
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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