Hydrochloric Acid → (R)-quinuclidin-3-yl 2-amino-2-phenylacetate

HRID 1619542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619542
C(OC([NH:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH2:14]1)=[O:11])=O)(C)(C)C.Cl>C1COCC1>[NH2:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:17][CH2:16][N:15]([CH2:20][CH2:19]2)[CH2:14]1)=[O:11]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 67425060(R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate

Produkt 1

HCID 59401091(R)-quinuclidin-3-yl 2-amino-2-phenylacetateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate (C1) (5.17 g, 14.3 mmol) was dissolved in THF (47.8 ml) and, while stirring at RT, 37% HCl (4.71 ml, 57.4 mmol) was added dropwise. The reaction was stirred at RT for 15 hours overnight. The solvent was evaporated, and the residue was dissolved in DCM/MeOH (9/1; 10 ml) and about 3 g of SiO2 was added. The solvent was evaporated, and the solid was loaded on a silica gel column and eluted with DCM/MeOH/NH4OH (9/1/0.1) to obtain (R)-quinuclidin-3-yl 2-amino-2-phenylacetate (2.23 g; 60% yield).

Aufarbeitung

  1. stirringThe reaction was stirred at RT for 15 hours overnight
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in DCM/MeOH (9/1; 10 ml)
  4. additionabout 3 g of SiO2 was added
  5. customThe solvent was evaporated
  6. washeluted with DCM/MeOH/NH4OH (9/1/0.1)

Quellen und Nachweise

ORD-Eintrag
ord-f0755640a23749989ff242643be29c1c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772314B2

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