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methyl 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoate → 2-(N-Boc-piperidine-4-yloxy)-4-(tert-butyl)benzoic acid

HRID 1445456
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1445456
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[CH:21][C:16]=2[C:17]([O:19]C)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[CH:21][C:16]=2[C:17]([OH:19])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 68532357methyl 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoate

Produkt 1

HCID 685305052-(N-Boc-piperidine-4-yloxy)-4-(tert-butyl)benzoic acidAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In a 50 ml RBF was suspended methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-tert-butylbenzoate (2.4 g, 6.1 mmol) in 25 ml of 3:1 THF:water to give a light emulsion, then was added solid LiOH monohydrate (567 mg, 13.5 mmol), the flask was fitted with a reflux condenser, and the mixture was heated at 50° C. with stirring for 16 h. The mixture was diluted with 75 ml water and washed twice with diethyl ether. The aqueous layer was acidified to about pH 2 with 1 N NaHSO4, and the resulting slurry extracted twice with 100 ml portions of EtOAc. The combined EtOAc layers were washed with brine, dried, then concentrated in vacuo to afford 2.1 g (91%) of the title acid as a brittle white foam.

Aufarbeitung

  1. customthe flask was fitted with a reflux condenser
  2. washwashed twice with diethyl ether
  3. extractionthe resulting slurry extracted twice with 100 ml portions of EtOAc
  4. washThe combined EtOAc layers were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ff9417e5950043d8a84ecf34d20bf9c1
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07666866B2

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