Methylparaben → HCID 58893828, compound

HRID 352745Notes

Reaction equation

HRID 352745 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][C@@H:21](O)[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][C@H:21]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

9

Reactant 5

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 58893828HCID 58893828, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In tetrahydrofuran (50 ml), methyl 4-hydroxybenzoate (1.01 g), (3R)-1-tert-butoxycarbonyl-3-pyrrolidinol (1.36 g) and triphenylphosphine (1.73 g) were dissolved, followed by the dropwise addition of a 40% solution (2.87 ml) of diethyl azodicarboxylate in toluene under ice cooling. The resulting mixture was stirred at room temperature for 20 hours. To the reaction mixture, ethyl acetate and a 10% aqueous solution of potassium carbonate were added to separate the organic layer. The organic layer so separated was washed with a 10% aqueous solution of potassium carbonate and water and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=2:1), whereby the title compound (1.60 g, 76%) was obtained.

Workup

  1. customto separate the organic layer
  2. customThe organic layer so separated
  3. washwas washed with a 10% aqueous solution of potassium carbonate and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=2:1), whereby the title compound (1.60 g, 76%)
  7. customwas obtained

Sources & evidence

ORD record
ord-ab1076dedd6448d6bbe9ebaed50ab236
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…