Hydrochloric Acid → tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylate

HRID 1527010

Reaktionsgleichung

Reaktionsgleichung von HRID 1527010
CC(C)([S@@]([NH:6][C@H:7]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)[CH3:8])=O)C.Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>CO>[NH2:6][CH:7]([CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:13][CH2:14]1)[CH3:8]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 117779509HCID 117779509, Verbindung

Produkt 1

HCID 22647295tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylateAusbeute 110,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a 1 L round bottomed flask charged with a magnetic stir bar was added crude tert-butyl 4-((S)-1-((S)-1,1-dimethylethylsulfinamido)ethyl)piperidine-1-carboxylate (29 g) was taken up in MeOH (200 mL) before addition of a 4 N solution of HCl in 1,4-dioxane (24.06 ml, 96 mmol). The resulting solution was then stirred at room temperature for 1 h at rt. The methanol was then removed in vacuo to afford viscous oil which was treated with sat'd aqueous NaHCO3 (˜500 mL) and extracted with ethyl acetate (2×500 mL). This organic phase was combined, dried with MgSO4, filtered, and solvent was then removed in vacuo affording the title compound (22 g) which was used without further purification.

Aufarbeitung

  1. additionTo a 1 L round bottomed flask charged with a magnetic stir bar
  2. customThe methanol was then removed in vacuo
  3. customto afford viscous oil which
  4. extractionextracted with ethyl acetate (2×500 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customsolvent was then removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8eef3beea22d4af69f787986754d9d2c
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085583B2

Verknüpfte Notizen

Wird geladen…