4-Methylmorpholine → (S)-1,3'-Bipyrrolidin-1'-YL(4-fluorophenyl)methanone

HRID 1176064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1176064
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN1CCOCC1.[N:18]1([C@H:23]2[CH2:27][CH2:26][NH:25][CH2:24]2)[CH2:22][CH2:21][CH2:20][CH2:19]1>ClC(Cl)C.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:25]2[CH2:26][CH2:27][C@H:23]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:24]2)=[O:8])=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 99734-Fluorobenzoic AcidHCID 7176274(3S)-3-(Pyrrolidin-1-YL)pyrrolidine

Produkt 1

HCID 59725829(S)-1,3'-Bipyrrolidin-1'-YL(4-fluorophenyl)methanoneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19746008DMF dichloroethaneLösungsmittel2×

Versuchsvorschrift

A solution of 4-fluorobenzoic acid (1.5 g, 10.71 mmol) in dichloroethane:DMF (4:1) was treated with O-benzotriazol-1-yl-N,N,N′N′-tetramethlyuronium tetrafluoroborate (4.13 gm 12.85 mmol) and N-methylmorpholine (5.41 g, 53.55 mmol) followed by a solution of (3′S)-1,3′-bipyrrolidine (2.52 g, 11.77 mmol) in dichloroethane:DMF (4:1). The reaction mixture was stirred at room temperature for 3 h and quenched with saturated sodium hydrogen carbonate. The phases were separated. The aqueous phase was extracted with ethyl acetate. The organic phase and the extracts were combined, washed sequentially with water and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash column chromatography to provide (3′S)-1′-(4-fluorobenzoyl)-1,3′-bipyrrolidine (57%) as a white solid.

Aufarbeitung

  1. customquenched with saturated sodium hydrogen carbonate
  2. customThe phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washwashed sequentially with water and saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6d6b8f2e0c0449b797e70ebed41c4fe4
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842715B2

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