Ethylparaben → ethyl 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoate

HRID 2422670Notes

Reaction equation

HRID 2422670 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.O[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]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>[CH2:9]([O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 11783050ethyl 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoateYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 4-hydroxybenzoate (4.15 g, 25.0 mmol), tert-butyl 4-hydroxytetrahydro-1(2H)-pyridinecarboxylate (5.0 g, 25.0 mmol) and triphenyl phosphine (7.87 g, 30.0 mmol) were dissolved in tetrahydrofuran (50 mL), and with stirring at 0° C., diisopropyl azodicarboxylate (6.06 g, 30.0 mmol) was added thereto and stirred for 24 hours. The reaction solution was concentrated, and the precipitated white solid was taken out through filtration and washed with ethyl acetate. The mother liquid was washed with aqueous 1 N sodium hydroxide solution and saturated saline water in that order, and the organic layer was dried with magnesium sulfate. The solvent was evaporated off, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1) to obtain the intended compound (5.45 g, 62%) as a colorless solid.

Workup

  1. stirringstirred for 24 hours
  2. concentrationThe reaction solution was concentrated
  3. filtrationthe precipitated white solid was taken out through filtration
  4. washwashed with ethyl acetate
  5. washThe mother liquid was washed with aqueous 1 N sodium hydroxide solution and saturated saline water in that order
  6. dry with materialthe organic layer was dried with magnesium sulfate
  7. customThe solvent was evaporated off
  8. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-35ab6affdc9345f5b626684df2fe7ca4
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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