Triphenylphosphine → HCID 68294314, compound

HRID 1850075Notes

Reaction equation

HRID 1850075 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:20]1[CH:24]=[C:23](/[CH:25]=[CH:26]/[C:27]([O:29][CH3:30])=[O:28])[CH:22]=[N:21]1.[CH3:31][N:32]1[CH2:37][CH2:36][CH:35]([CH2:38]O)[CH2:34][CH2:33]1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[CH3:31][N:32]1[CH2:37][CH2:36][CH:35]([CH2:38][N:20]2[CH:24]=[C:23](/[CH:25]=[CH:26]/[C:27]([O:29][CH3:30])=[O:28])[CH:22]=[N:21]2)[CH2:34][CH2:33]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 2719711-Methyl-4-piperidinemethanolHCID 68295278HCID 68295278, compound

Product 1

HCID 68294314HCID 68294314, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (393 mg, 1.5 mmol) and (E)-methyl 3-(1H-pyrazol-4-yl)acrylate, prepared as described above, (12 mg, 1 mmol) were added to a solution of N-methyl-4-hydroxymethyl-piperidine (165 mg, 1.25 mmol) in tetrahydrofuran (THF, 2 mL). After addition of di-tert-butyl azodicarboxylate (345 mg, 1.5 mmol), the reaction was stirred overnight at room temperature. Solvents were evaporated under reduced pressure and the residue was purified by silica gel chromatography using a gradient of Hexane in EtOAc from 1:1 to 0:100 v/v. Fractions containing product were pooled and evaporated to give 220 mg of pure material (0.84 mmol, 84%).

Workup

  1. customSolvents were evaporated under reduced pressure
  2. customthe residue was purified by silica gel chromatography
  3. additionFractions containing product
  4. customevaporated

Sources & evidence

ORD record
ord-eb1833eaac4b4f5d9df9114d5309d980
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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