Triphenylphosphine → HCID 22933993, compound

HRID 1269729Notes

Reaction equation

HRID 1269729 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.O[CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1014381H-Indazol-5-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22933993HCID 22933993, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1H-indazol-5-ol (134 mg, 0.999 mmol) in tetrahydrofuran (4 ml) were added tert-butyl 4-hydroxy-1-piperidinecarboxylate (201 mg, 0.999 mmol) and triphenylphosphine (262 mg, 0.999 mmol) at room temperature, followed by adding thereto diethyl azodicarboxylate (0.46 ml, 1.01 mmol) at 0° C., and the resulting mixture was stirred at 0° C. for 30 minutes and then at room temperature for 4 hours. Subsequently, the solvent of the reaction mixture was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=7/3) to obtain tert-butyl 4-(1H-indazol-5-yloxy)-1-piperidinecarboxylate (77 mg, 24%).

Workup

  1. additionby adding
  2. distillationSubsequently, the solvent of the reaction mixture was distilled off under reduced pressure
  3. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-247321dac6334a29a0b4ada20887ca82
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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