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Sodium Hydroxide → 3-{1-[(Tert-butoxy)carbonyl]pyrrolidin-3-yl}benzoic acid

HRID 880289
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 880289
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[OH-].[Na+]>CCO.O>[C:19]([O:18][C:16]([N:13]1[CH2:14][CH2:15][CH:11]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([OH:4])=[O:2])[CH2:12]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 90239134Tert-butyl 3-(3-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 534066233-{1-[(Tert-butoxy)carbonyl]pyrrolidin-3-yl}benzoic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
29 °C

Versuchsvorschrift

To a solution of tert-butyl 3-(3-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylate (210 mg, 0.7 mmol) in EtOH (4 ml) was added a solution of NaOH (56 mg, 1.4 mmol) in H2O (1 ml) at 29° C. The mixture was stirred for 30 min at 29° C. The mixture was concentrated and the residue was treated with water and extracted with EA. The water layer was treated with 2N HCl until pH=3, extracted with EA and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification (200 mg, Yield 98.0%).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additionthe residue was treated with water
  3. extractionextracted with EA
  4. additionThe water layer was treated with 2N HCl until pH=3
  5. extractionextracted with EA
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b932856dad9c421abc16f4d6bdf5ed55
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08993555B2

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