Sodium Hydroxide → (2R,3R)-1-(tert-Butoxycarbonyl)-2-phenylpyrrolidine-3-carboxylic acid

HRID 130621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 130621
C([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:7]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:5])C.[OH-].[Na+]>CO>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C@@H:6]([C:4]([OH:5])=[O:3])[C@@H:7]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 131726910HCID 131726910, Verbindung

Produkt 1

HCID 57354967(2R,3R)-1-(tert-Butoxycarbonyl)-2-phenylpyrrolidine-3-carboxylic acidAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

trans-2-Phenyl-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (obtained from preparatory example 3) (0.68 g, 2.13 mmol) was stirred in a solution of 10.5 mL of 1M NaOH and 10.5 mL of methanol at rt for 2 days. The mixture was concentrated, acidified with 6 M HCl (aq) to pH ˜2, and extracted 3× with CH2Cl2. The combined extracts were dried through cotton, and concentrated. Silica gel chromatography eluting with hexanes/ethyl acetate (1:1) gave 0.58 g of a colorless oil. Crystallization from pet. ether/ether (ca. 10:1; 25 mL) gave 0.427 g (69%) of the title compound. MS APCI: [M+H]+=292.1

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. extractionextracted 3× with CH2Cl2
  3. customThe combined extracts were dried through cotton
  4. concentrationconcentrated
  5. washSilica gel chromatography eluting with hexanes/ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0a87de974337438d98142cca5a5cdfcc
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381741B2

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