tert-Butyl 4-(2-bromoethyl)piperazine-1-carboxylate → Tert-butyl 4-(2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)ethyl)piperazine-1-carboxylate

HRID 1667130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667130
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH2:12][CH2:11][NH:10][C:9]2=[O:13])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]1>O1CCCC1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][N:10]([CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:32][CH2:31]3)[C:9]2=[O:13])=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 15946441tert-Butyl 4-(2-bromoethyl)piperazine-1-carboxylateHCID 23665647Potassium tert-butoxideHCID 673585653,3-Bis(4-fluorophenyl)pyrrolidin-2-one

Produkt 1

HCID 67359885Tert-butyl 4-(2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)ethyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of 3,3-bis(4-fluorophenyl)pyrrolidin-2-one (Example 58B, 1.37 g, 5.00 mmol) in tetrahydrofuran (30 mL) was added potassium t-butoxide (1.0 M in tetrahydrofuran) (7.5 mL, 7.5 mmol) followed by the product from Example 63A (1.47 g, 5.00 mmol). The reaction mixture was heated at 75° C. for 18 hours. The reaction was concentrated, diluted with ethyl acetate, washed with water and brine, dried with MgSO4, filtered and concentrated. The residue was purified with silica gel chromatography eluting with 3% methanol/dichloromethane to give the title compound. MS (DCI) m/z 486.3 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel chromatography
  8. washeluting with 3% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-2e93e0abe194410db3b05be3b3510765
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044069B2

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