Triphenylphosphine → HCID 67359917, compound

HRID 1465008Notes

Reaction equation

HRID 1465008 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].O[CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[CH3:23][N:20]1[CH2:21][CH2:22][CH:17]([O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[C:12]([F:13])([F:14])[F:15])[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 660484-Piperidinol, 1-methyl-HCID 5363146Diisopropyl azodicarboxylateHCID 13962148Methyl 4-hydroxy-3-(trifluoromethyl)benzoate

Product 1

HCID 67359917HCID 67359917, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask wrapped with foil, methyl 4-hydroxy-3-(trifluoromethyl)benzoate (500 mg, 2.13 mmol) was dissolved in methylene chloride (10 mL). 4-Hydroxy-1-methyl-piperidine (0.25 mL, 2.13 mmol), PPh3 (670 mg, 2.56 mmol), and DIAD (0.50 mL, 2.56 mmol) were added thereto, and the mixture was stirred at room temperature for 23 hours. DTAD (4.26 mmol) and PPh3 (1.12 g, 4.26 mmol) were added at 0° C. to the reaction mixture, which was stirred at room temperature for 24 hours. The resulting mixture was concentrated and then purified by silica gel chromatography (Hex/EA=1/1→DCM/MeOH=10/1) to obtain the title compound (512 mg, 76%).

Workup

  1. stirringwas stirred at room temperature for 24 hours
  2. concentrationThe resulting mixture was concentrated
  3. custompurified by silica gel chromatography (Hex/EA=1/1→DCM/MeOH=10/1)

Sources & evidence

ORD record
ord-6c198f8679f3412aa7f9c32c5dc2c004
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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