Sodium Thiosulfate → HCID 68503284, compound

HRID 1176643Notes

Reaction equation

HRID 1176643 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.S([O-])([O-])(=O)=S.[Na+].[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 24477Sodium ThiosulfateHCID 27339311,1'-Difluoro-2,2'-bipyridinium Bis(tetrafluoroborate)HCID 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 thiosulphate 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-ca9557d534c64cdba2e7c28009256e08
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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