Triphenylphosphine → HCID 58216786, compound

HRID 513138Notes

Reaction equation

HRID 513138 reaction equation
CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C.[OH:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24](=[O:26])[CH3:25])[CH2:20][CH2:19]1.[CH3:27][O:28][C:29](=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:27][O:28][C:29](=[O:38])[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=1[O:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24](=[O:26])[CH3:25])[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 89719Methyl (2-hydroxyphenyl)acetateHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-one

Product 1

HCID 58216786HCID 58216786, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Di-tert-butylazodicarboxylate (305 mg, 1.32 mmol) was dropped to a solution of 1-(4-hydroxy-piperidin-1-yl)-ethanone (259 mg, 1.8 mmol) in tetrahydrofuran (4 mL) under nitrogen atmosphere. Then (2-hydroxy-phenyl)-acetic acid methyl ester (200 mg, 1.2 mmol) and triphenylphosphine (347 mg, 1.3 mmol) were added. The yellow mixture was stirred at 20° C. for 16 h. The solvent was evaporated and the residue was purified on silica using hexane/ethyl acetate mixture of increasing polarity (from 70% to 100% ethyl acetate) as eluent to give 195 mg (55.6%) of a colourless oil.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified on silica
  3. additionhexane/ethyl acetate mixture
  4. temperatureof increasing polarity (from 70% to 100% ethyl acetate) as eluent

Sources & evidence

ORD record
ord-75d37b1e90234212ba874b6519345825
Source dataset
uspto-grants-2015_08
Patent number
US09102679B2

Reaction notes

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