4-(Bromoacetyl)benzonitrile → (R)-ethyl 2-(1-(2-(4-cyanophenyl)-2-oxoethyl)piperidin-3-yl)acetate

HRID 1948490Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948490
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=[O:4].[NH:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]1>C1(C)C=CC=CC=1>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([C:3](=[O:4])[CH2:2][N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]2)=[CH:6][CH:7]=1)#[N:10]

Komponenten

4

Edukt 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 7161133ethyl 2-[(3R)-piperidin-3-yl]acetate

Produkt 1

HCID 58374115(R)-ethyl 2-(1-(2-(4-cyanophenyl)-2-oxoethyl)piperidin-3-yl)acetateAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 4-(2-bromoacetyl)benzonitrile (5.5g, 24.55 mmol) in toluene was added (R)-ethyl 2-(piperidin-3-yl)acetate (4 g, 23.36 mmol). The reaction mixture was stirred for 4 days at room temperature and then stirred from one day at 50° C. Solvents were removed in vacuo. The resulting solids were triturated with EtOAc. The solid material was filtered and washed with EtOAc. The solid material was collected and dried to yield 5 g of (R)-ethyl 2-(1-(2-(4-cyanophenyl)-2-oxoethyl)piperidin-3-yl)acetate. MS (M+1)=314. HPLC Peak RT=0.77 minutes.

Aufarbeitung

  1. stirringstirred from one day at 50° C
  2. customSolvents were removed in vacuo
  3. customThe resulting solids were triturated with EtOAc
  4. filtrationThe solid material was filtered
  5. washwashed with EtOAc
  6. customThe solid material was collected
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8dce0bb7f8e54713a7240acfeed0ccf8
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399451B2

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