3-Hydroxyacetophenone → HCID 86670542, compound

HRID 2170840Notes

Reaction equation

HRID 2170840 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.O[C:16]1[CH:17]=[C:18]([C:22](=[O:24])[CH3:23])[CH:19]=[CH:20][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.O>[C:22]([C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)(=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 84873-HydroxyacetophenoneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 86670542HCID 86670542, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (4.00 g, 19.9 mmol), 1-(3-hydroxyphenyl)ethanone (2.71 g, 19.9 mmol), and triphenylphosphine (5.73 g, 21.9 mmol) in tetrahydrofuran (100 mL) was added slowly diisopropyl azodicarboxylate (4.25 mL, 21.9 mmol) at 0° C. under Nitrogen. The resulting mixture was stirred at room temperature for 17 hours. The mixture was poured into water (200 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with water (200 mL) and dried over sodium sulfate. After removal of the solvent, the residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (4:1) to give 4.70 g (74%) of the title compound as colorless oil.

Workup

  1. extractionextracted with ethyl acetate (200 mL)
  2. washThe organic layer was washed with water (200 mL)
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-c8f6b83127a64743b51bf35054395964
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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