Triphenylphosphine → 4-[3-(3-Nitro-phenyl)-4-pyridin-4-yl-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1843605Notes

Reaction equation

HRID 1843605 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[CH:13][NH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][CH:50](O)[CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:42])[CH3:41].CCOC(/N=N/C(OCC)=O)=O.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][CH:50]([N:12]2[CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:11]2)[CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:41])[CH3:42]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 178526612HCID 178526612, compound

Product 1

HCID 671840714-[3-(3-Nitro-phenyl)-4-pyridin-4-yl-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-[3-(3-nitro-phenyl)-1H-pyrazol-4-yl]-pyridine (200 mg, 0.750 mmol) in anhydrous tetrahydrofuran (3 mL) at 0° C. triphenylphosphine (293 mg, 1.12 mmol, 1.5 eq), 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (150 mg, 0.750 mmol, 1 eq) and DEAD (176 μL, 1.12 mmol, 1.5 eq) were added. The reaction was allowed to warm to room temperature and stirred under nitrogen atmosphere overnight. The regioisomeric ratio was 1:4 at 254 nm in favor of the N1-alkylated product. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (DCM/ethanol 97:3) to give 950 mg of major regioisomer contaminated with triphenylphosphinoxide.

Workup

  1. additionwere added
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (DCM/ethanol 97:3)
  4. customto give 950 mg of major regioisomer

Sources & evidence

ORD record
ord-6f1ca0bdcdcf4fc3a65086352d29c924
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

Loading…