Triphenylphosphine → HCID 58305827, compound

HRID 1878307Notes

Reaction equation

HRID 1878307 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].O[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[C:29]=1[C:36](=[O:38])[CH3:37].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:36]([C:29]1[C:30]([O:34][CH3:35])=[CH:31][CH:32]=[CH:33][C:28]=1[O:15][CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])(=[O:38])[CH3:37]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 697091-(2-Hydroxy-6-methoxyphenyl)ethan-1-oneHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 58305827HCID 58305827, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (2.82 g, 14.0 mmol) is added to a stirred solution of tert-butyl 3-hydroxypropylcarbamate (2.45 g, 14.0 mmol), 1-(2-hydroxy-6-methoxyphenyl)ethanone (1.94 g, 11.7 mmol) and triphenylphosphine (3.66 g, 14.0 mmol) in THF (50 mL) at room temperature. After stirring for 18 h, the solvent is removed under reduced pressure and the crude product is chromatographed (hexane-ethyl acetate: 0-60% gradient) to afford 1.60 g of the title compound.

Workup

  1. customthe solvent is removed under reduced pressure
  2. customthe crude product is chromatographed (hexane-ethyl acetate: 0-60% gradient)

Sources & evidence

ORD record
ord-782a9eba264e470cb4e98501c790c276
Source dataset
uspto-grants-2012_11
Patent number
US08314108B2

Reaction notes

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