Triphenylphosphine → HCID 67249460, compound

HRID 1035317Notes

Reaction equation

HRID 1035317 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:14][CH2:15][OH:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1O.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:14][CH2:15][O:16][C:19]2[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:18]=2[Br:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 134938392-Bromo-5-methoxyphenolHCID 23395653(S)-2-(4-benzylpiperazin-2-yl)ethanol

Product 1

HCID 67249460HCID 67249460, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask was charged with (S)-2-(4-benzylpiperazin-2-yl)ethanol (1.0 g, 4.5 mmol), 2-bromo-5-methoxyphenol (1.0 g, 5.0 mmol), di-tert-butyl azodicarboxylate (1.57 g, 6.81 mmol), polymer-supported triphenylphosphine resin (4.354 g, 9.08 mmol) and tetrahydrofuran (30 mL). The reaction stirred for 16 hours. The resin was removed via filtration and the solution was concentrated. Purification via flash chromatography (0-30% methanol/dichloromethane) afforded the title compound.

Workup

  1. customThe resin was removed via filtration
  2. concentrationthe solution was concentrated
  3. customPurification via flash chromatography (0-30% methanol/dichloromethane)

Sources & evidence

ORD record
ord-f2b07ba9ae2f4f408845e2342972110a
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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