Triphenylphosphine → HCID 58270746, compound

HRID 222254Notes

Reaction equation

HRID 222254 reaction equation
O[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:9])[CH2:4][CH2:3]1.[C:17]1([C:23]2[NH:27][N:26]=[N:25][N:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.C1COCC1>[C:17]1([C:23]2[N:24]=[N:25][N:26]([CH:2]3[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]4[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=4)=[O:9])[CH2:4][CH2:3]3)[N:27]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58270786HCID 58270786, compoundHCID 178418369HCID 178418369, compound

Product 1

HCID 58270746HCID 58270746, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of pyridin-3-yl 4-hydroxypiperidine-1-carboxylate (300 mg), 5-phenyl-1H-tetrazole (217 mg), triphenyl phosphine (460 mg), and THF (3 mL) was added dropwise a 2.2 M solution of diethyl azodicarboxylate in toluene (0.8 mL), followed by stirring at room temperature overnight. The reaction liquid was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=99/1 to 90/10), and purified again by silica gel column chromatography (hexane/ethyl acetate=70/30 to 0/100). To the purified product was added hexane/ethyl acetate, followed by stirring, and then the resulting solid was collected by filtration and dried to obtain pyridin-3-yl 4-(5-phenyl-2H-tetrazol-2-yl)piperidine-1-carboxylate (250 mg) as a colorless solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (chloroform/methanol=99/1 to 90/10)
  4. custompurified again by silica gel column chromatography (hexane/ethyl acetate=70/30 to 0/100)
  5. additionTo the purified product was added hexane/ethyl acetate
  6. stirringby stirring
  7. filtrationthe resulting solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-8a5e6dfe2de1403ba1c51f9315cff52c
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

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