Triphenylphosphine → HCID 68679430, compound

HRID 2265877Notes

Reaction equation

HRID 2265877 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[C:21]([OH:26])[CH:22]=4)[CH:17]3[C:27]([O:29][CH3:30])=[O:28])(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:64][N:65]1[CH2:70][CH2:69][N:68]([CH2:71][CH2:72][CH2:73]O)[CH2:67][CH2:66]1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([S:13]([N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[C:21]([O:26][CH2:73][CH2:72][CH2:71][N:68]5[CH2:69][CH2:70][N:65]([CH3:64])[CH2:66][CH2:67]5)[CH:22]=4)[CH:17]3[C:27]([O:29][CH3:30])=[O:28])(=[O:14])=[O:15])=[CH:11][CH:12]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 792083-(4-Methyl-1-piperazine)propan-1-olHCID 5462977Diethyl azodicarboxylateHCID 68679822Methyl 2-[4-(4-fluorophenoxy)benzenesulfonyl]-6-hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylate

Product 1

HCID 68679430HCID 68679430, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

250 mg (0.55 mmol) of methyl 2-[4-(4-fluorophenoxy)benzenesulfonyl]-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxlate are dissolved in 5 ml of THF. At room temperature, 216 mg (0.825 mmol) of triphenylphosphine, 142 μl (0.825 mmol) of DEAD and 120 mg (0.825 mmol) of 3-(4-methylpiperazin-1-yl)propan-1-ol are added, and the solution is stirred at room temperature for 18 hours. The solvent is then removed, and the residue is chromatographed on silica gel, allowing the desired product to be isolated as a colorless solid. Yield 76%.

Workup

  1. customThe solvent is then removed
  2. customthe residue is chromatographed on silica gel
  3. customto be isolated as a colorless solid

Sources & evidence

ORD record
ord-e929eec59fae4e6f8affd41005073166
Source dataset
uspto-grants-2010_12
Patent number
US07858619B2

Reaction notes

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