Triphenylphosphine → HCID 178470582, compound

HRID 1860647Notes

Reaction equation

HRID 1860647 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([N:16]1[CH2:21][CH2:20][CH2:19][C:18]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[CH2:17]1)(=[O:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:56][CH2:57][CH2:58][NH:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][N+:61]=1[O-:66]>C1COCC1>[C:13]([N:16]1[CH2:21][CH2:20][CH2:19][C:18]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:56][CH2:57][CH2:58][NH:59][C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][N+:61]=3[O-:66])=[CH:27][CH:28]=2)[CH2:17]1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 60074796Ethyl [1-acetyl-3-(4-hydroxybenzyl)piperidin-3-yl]acetateHCID 178526251HCID 178526251, compound

Product 1

HCID 178470582HCID 178470582, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Diethyl azodicarboxylate (267 mg, 1.53 mmol) was added to a solution of the product from STEP 8 (348 mg, 1.09 mmol) and triphenylphosphine (437 mg, 1.66 mmol) in 3.9 ml THF at 0° C. and stirred for 15 min. 2-(3-Hydroxypropylamino)pyridine N-oxide (418 mg, 2.48 mmol) was added. The reaction was warmed to 40° C. After 15 min, the reaction was cooled to room temperature and stirred for 18 h. The reaction was concentrated and the residue was purified by chromatography (on silica gel, dichloromethane/2-propanol/acetic acid=95/5/0.5) to give a product mixture in 406 mg. The 1H NMR spectrum of the product was consistent for the proposed structure.

Workup

  1. waitAfter 15 min
  2. temperaturethe reaction was cooled to room temperature
  3. stirringstirred for 18 h
  4. concentrationThe reaction was concentrated
  5. customthe residue was purified by chromatography (on silica gel, dichloromethane/2-propanol/acetic acid=95/5/0.5)
  6. customto give a product mixture in 406 mg

Sources & evidence

ORD record
ord-5820056deab64f06bfecb0659fd80510
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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