Hydrochloric Acid → 1-(alpha-methylbenzyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

HRID 323441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323441
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[CH2:11]([O:13][CH2:14][CH2:15][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[NH:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][C:34]2([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:38][CH2:37][NH:36][CH2:35]2)[CH2:28][CH2:27]1)[CH3:12].C([BH3-])#N.[Na+].Cl>CO.BrCOC1C(O)=CC=C(C)C=1.C(OCC)(=O)C>[CH3:2][CH:1]([N:36]1[CH2:37][CH2:38][C:34]([CH2:33][CH2:32][N:29]2[CH2:30][CH2:31][CH:26]([NH:25][C:17]3[N:16]([CH2:15][CH2:14][O:13][CH2:11][CH3:12])[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=3)[CH2:27][CH2:28]2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:35]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 5003444Sodium cyanoborohydrideHCID 220090993-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid salt

Produkt 1

HCID 178956821-(alpha-methylbenzyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 86612474BromocreosolKatalysatorHCID 887MethanolLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

According to the method of J. Am. Chem. Soc., 93, 2897 (1971), combine acetophenone (10 mmol) and 3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid salt (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt) (10 mmol) in methanol (100 mL). Add bromocreosol green (0.5% by weight in methanol, 1 drop). Add dropwise, a solution of sodium cyanoborohydride (10 mL, 1M in tetrahydrofuran, 10 mmol) and at the same time maintain the pH of the reaction mixture, as indicated by a yellow color for the indicator, by the addition of a 5 M solution of hydrochloric acid in methanol. When the reaction is complete, concentrate the reaction mixture in vacuo to obtain a residue. Dilute the residue with ethyl acetate and extract with water. Separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound.

Aufarbeitung

  1. additionAdd dropwise
  2. concentrationconcentrate the reaction mixture in vacuo
  3. customto obtain a residue
  4. extractionextract with water
  5. customSeparate the layers
  6. dry with materialdry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-394e22d4ba0b463b95ef6450faf46722
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211199B1

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