Trifluoroacetic acid → benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl ester

HRID 1517065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517065
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][CH2:16][C@H:15]2[CH2:19][O:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][CH2:16][C@H:15]2[CH2:19][O:20][C:21](=[O:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:10][CH2:9]1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 669015494-((S)-2-Benzoyloxymethyl-pyrrolidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 66901590benzoic acid (S)-1-piperidin-4-yl-pyrrolidin-2-ylmethyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2.78 g (7.2 mmol) of 4-((S)-2-benzoyloxymethyl-pyrrolidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester in 80 ml of CH2Cl2 was added 5.83 ml of TFA (90% in water) drop by drop. After 16 hours, the reaction mixture was poured into crashed ice; then, the pH was adjusted to 9-10 with sodium carbonate solution and the mixture was extracted three times with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography [CH2Cl2 (sat. with NH3)/MeOH 1:0 to 9:1] to give 1.96 g (95%) of the title compound as yellow oil. MS: 289.1 (MH+).

Aufarbeitung

  1. additionthe reaction mixture was poured
  2. extractionthe mixture was extracted three times with CH2Cl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography [CH2Cl2 (sat. with NH3)/MeOH 1:0 to 9:1]

Quellen und Nachweise

ORD-Eintrag
ord-f1c8466dea384f14b48a24635363b7a6
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227613B2

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