Racemic (2'S,3S,4'R)-4'-[5-bromo-2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-phenyl]-6-chloro-2'-(3-fluorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione → Racemic (2'S,3S,4'R)-4'-[5-bromo-2-(4-piperidinyloxy)-phenyl]-6-chloro-2'-(5-fluorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504505
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH:33]2[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]2)=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=3)[C:9]32[C:29]2[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[NH:23][C:22]3=[O:31])[CH:7]=1>C(O)(C(F)(F)F)=O.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:16]=[C:17]([F:21])[CH:18]=[CH:19][CH:20]=3)[C:9]32[C:29]2[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[NH:23][C:22]3=[O:31])[CH:7]=1

Komponenten

4

Edukt 1

HCID 74928441Racemic (2'S,3S,4'R)-4'-[5-bromo-2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-phenyl]-6-chloro-2'-(3-fluorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Produkt 1

HCID 74928442Racemic (2'S,3S,4'R)-4'-[5-bromo-2-(4-piperidinyloxy)-phenyl]-6-chloro-2'-(5-fluorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of racemic (2′S,3S,4′R)-4′-[5-bromo-2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-phenyl]-6-chloro-2′-(3-fluorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.35 g, 0.5 mmol) in TFA (2 mL) and dichloromethane (2 mL) was stirred at r.t. for 0.5 h. The solution was diluted with DCM, washed with 1N Na2CO3 aq. (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, concentrated to give title compound as a yellow solid (Yield: 0.21 g, 70%).

Aufarbeitung

  1. washwashed with 1N Na2CO3 aq. (50 mL) and brine (50 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c763e1c86e5e42538e0bde142eb20a8a
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776875B2

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