Acetic Acid → 1'-[(6-Chloro-1-{[(3S)-1-methylpiperidin-3-yl]methyl}-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4'-piperidine]

HRID 2055541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2055541
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]([N:20]3[CH2:25][CH2:24][C:23]4([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=5[CH2:27][O:26]4)[CH2:22][CH2:21]3)=[O:19])=[CH:7][N:8]2[CH2:11][C@H:12]2[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]2)=[CH:4][CH:3]=1.[CH3:34]C(O)=O.[BH3-]C#N.[Na+]>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]([N:20]3[CH2:21][CH2:22][C:23]4([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=5[CH2:27][O:26]4)[CH2:24][CH2:25]3)=[O:19])=[CH:7][N:8]2[CH2:11][C@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([CH3:34])[CH2:13]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 596575381'-({6-Chloro-1-[(3S)-piperidin-3-ylmethyl]-1H-indol-3-yl}carbonyl)-3H-spiro[2-benzofuran-1,4'-piperidine]

Produkt 1

HCID 596575681'-[(6-Chloro-1-{[(3S)-1-methylpiperidin-3-yl]methyl}-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4'-piperidine]

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 1′-({6-chloro-1-[(3S)-piperidin-3-ylmethyl]-1H-indol-3-yl}carbonyl)-3H-spiro[2-benzofuran-1,4′-piperidine] in MeOH was treated with aq. H2CO (1.5 eq), AcOH (1.1 eq) and stirred for 15 min at room temperature, then treated with NaCNBH3 (1.1 eq) and stirred at room temperature for 1 h. Concentration and purification by preparative HPLC the desired product. ES-MS m/e (%): 478.2(M+H+).

Aufarbeitung

  1. stirringstirred at room temperature for 1 h
  2. concentrationConcentration and purification by preparative HPLC the desired product

Quellen und Nachweise

ORD-Eintrag
ord-dcd3ef4d50794247adb8066bb8f9494b
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07332501B2

Notizen zur Reaktion

Wird geladen…