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

HRID 747772Notes

Reaction equation

HRID 747772 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.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23](O)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1.C(OCC)(=O)C>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 11783050ethyl 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.7 g (10.2 mmol) of ethyl 4-hydroxybenzoate, 1.76 g (9.3 mmol) of 1-t-butoxycarbonyl-4-hydroxypiperidine, and 2.44 g (9.3 mmol) of triphenyl phosphine were dissolved in 40 ml of tetrahydrofuran, and 1.62 g (9.3 mmol) of diethyl azodicarboxylic acid was added thereto, and they were stirred at room temperature overnight. It was treated in an ordinary manner by treatment with ethyl acetate as the extractant to obtain the crude product. Then, it was purified by silica gel column chromatography to obtain the title compound.

Workup

  1. customto obtain the crude product
  2. customThen, it was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3281eda9177f414c8e937ef297284e13
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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