Triphenylphosphine → HCID 67067087, compound

HRID 2074271Notes

Reaction equation

HRID 2074271 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:35]=[CH:34][C:17]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[O:26])[CH2:21][CH2:20]2)=[CH:16][CH:15]=1.[Cl:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH2:40]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl.C1COCC1>[ClH:36].[Cl:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH2:40][O:13][C:14]1[CH:35]=[CH:34][C:17]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[O:26])[CH2:21][CH2:20]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 701173-Chlorobenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 670670763-Pyridyl 4-(4-hydroxyphenoxy)-1-piperidinecarboxylate

Product 1

HCID 67067087HCID 67067087, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.35 ml, 40% Tol solution) was dropwise added to a THF (5 ml) solution containing 3-pyridyl 4-(4-hydroxyphenoxy)-1-piperidinecarboxylate (160 mg), 3-chlorobenzyl alcohol (110 mg) and triphenylphosphine (200 mg) at 0° C., followed by stirring at room temperature for 24 hours. The reaction solution was diluted with chloroform, washed with aqueous saturated sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=1:3 (v/v)). The resulting oil was dissolved in EtOAc (5 ml), and 4 M hydrogen chloride/EtOAc solution (1 ml) was added thereto, followed by stirring at room temperature. The solvent was evaporated under reduced pressure, and the precipitated solid was recrystallized from EtOAc/2-propanol to obtain 3-pyridyl 4-{4-[(3-chlorobenzyl)oxy]phenoxy}-1-piperidinecarboxylate hydrochloride (45 mg).

Workup

  1. washwashed with aqueous saturated sodium hydrogencarbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=1:3 (v/v))
  5. dissolutionThe resulting oil was dissolved in EtOAc (5 ml)
  6. addition4 M hydrogen chloride/EtOAc solution (1 ml) was added
  7. stirringby stirring at room temperature
  8. customThe solvent was evaporated under reduced pressure
  9. customthe precipitated solid was recrystallized from EtOAc/2-propanol

Sources & evidence

ORD record
ord-91c5b379be4b4361bb3f9ea6056f6c1d
Source dataset
uspto-grants-2011_04
Patent number
US07919494B2

Reaction notes

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