Lithium hydroxide, monohydrate → (6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid

HRID 1424673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424673
[CH2:1]1[C:3]2([CH2:7][C@@H:6]([C:8]([O:10]C)=[O:9])[N:5]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4]2)[CH2:2]1.O[Li].O>C(O)C.O>[C:15]([O:14][C:12]([N:5]1[C@H:6]([C:8]([OH:10])=[O:9])[CH2:7][C:3]2([CH2:2][CH2:1]2)[CH2:4]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 57611019(S)-5-tert-Butyl 6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate

Produkt 1

HCID 39871141(6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acidAusbeute 102,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of (S)-5-tert-butyl 6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate (0.436 g, 1.708 mmol) in ethanol (4 mL) was added a solution of LiOH.H2O (86.0 mg, 2.049 mmol, 1.2 eq) in H2O (2 mL) at room temperature. The mixture was stirred at room temperature for 20 hours. EtOH was removed by rotavapor. The aqueous residue was diluted with H2O and extracted with Et2O. The aqueous layer was cooled with an ice bath and acidified to pH ˜2 with 1 N HCl. The resulting milky solution was extracted with a mixed solvent of EtOAc and CH2Cl2. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was dried under vacuum to afford the desired product as an off-white solid (0.422 g, 100%).

Aufarbeitung

  1. customEtOH was removed by rotavapor
  2. additionThe aqueous residue was diluted with H2O
  3. extractionextracted with Et2O
  4. temperatureThe aqueous layer was cooled with an ice bath
  5. extractionThe resulting milky solution was extracted with a mixed solvent of EtOAc and CH2Cl2
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c274e61221014342aff2189a69d50366
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927739B2

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