Morpholine → HCID 58805171, compound

HRID 884456Notes

Reaction equation

HRID 884456 reaction equation
[C:1]([C:4]1[C:9]([OH:10])=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[CH:6][C:5]=1[OH:19])(=[O:3])[CH3:2].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[OH:19][C:5]1[CH:6]=[C:7]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:8]=[C:9]([OH:10])[C:4]=1[C:1](=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 62657Potassium Phosphate, TribasicHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 58805195HCID 58805195, compound

Product 1

HCID 58805171HCID 58805171, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of trifluoromethanesulfonic acid 4-acetyl-3,5-dihydroxy-phenyl ester (1.0 g, 3.33 mmol), morpholine (0.35 mL, 3.99 mmol), tris-(dibenzylideneacetone) dipalladium(0) (153 mg, 0.167 mmol), biphenyl-2-yl-di-tert-butyl-phosphane (198 mg, 0.666 mmol), and K3PO4 (1.41 mg, 6.66 mmol) in THF (2 mL) was heated to 85° C. in a sealed tube for 2 h. The reaction mixture was allowed to cool to room temperature, and filtered through a ¾″ silica gel (60 Å) plug. The plug was washed with EtOAc (75 mL) and the filtrate concentrated. The concentrate was purified via Biotage chromatography with gradient elution from 100% hexanes to 40% EtOAc/hexanes to yield 475 mg (60%) of 1-(2,6-dihydroxy-4-morpholin-4-yl-phenyl)-ethanone. Rf=0.16 (50% EtOAc/hexanes).

Workup

  1. filtrationfiltered through a ¾″ silica gel (60 Å) plug
  2. washThe plug was washed with EtOAc (75 mL)
  3. concentrationthe filtrate concentrated
  4. customThe concentrate was purified via Biotage chromatography with gradient elution from 100% hexanes to 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-7438dd081919440dba85624abd3059c6
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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