Acetic Acid → 4-Azetidin-1-yl-1-benzyl-piperidine

HRID 644355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 644355
C(O)(=O)C.[CH2:5]([N:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:19]1[CH2:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[N:19]1([CH:15]2[CH2:16][CH2:17][N:12]([CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:13][CH2:14]2)[CH2:22][CH2:21][CH2:20]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 10422AzetidineHCID 192201-Benzyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 231533994-Azetidin-1-yl-1-benzyl-piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.0 mL (17.5 mmol) glacial acetic acid were added to the stirred mixture of 3.0 mL (16.5 mmol) 1-benzyl-4-piperidone, 1.0 g (17.5 mmol) azetidine and 100 mL DCM. Then 6.0 g (39.5 mmol) sodium triacetoxy-borohydride was added batchwise within one hour while cooling with an ice bath and the mixture was stirred for a further 12 h at RT. The reaction mixture was extracted with 200 mL EtOAc, the organic phase was dried, evaporated down under reduced pressure and the residue was purified by chromatography.

Aufarbeitung

  1. temperaturewhile cooling with an ice bath
  2. extractionThe reaction mixture was extracted with 200 mL EtOAc
  3. customthe organic phase was dried
  4. customevaporated down under reduced pressure
  5. customthe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-17b4b0f35ba7457796189530db10e900
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700589B2

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