tert-Butyl bromoacetate → Dimethyl (2s,3s,5s)-5-(2-tert-butoxy-2-oxoethoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

HRID 535073

Reaktionsgleichung

Reaktionsgleichung von HRID 535073
[OH:1][C@@H:2]1[CH2:7][N:6]([C:8]([O:10][CH3:11])=[O:9])[C@H:5]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[C@@H:4]([C:26]([O:28][CH3:29])=[O:27])[CH2:3]1.CC(C)([O-])C.[K+].[CH3:36][C:37]([O:40][C:41](=[O:44])[CH2:42]Br)([CH3:39])[CH3:38]>O1CCCC1>[C:37]([O:40][C:41](=[O:44])[CH2:42][O:1][C@@H:2]1[CH2:7][N:6]([C:8]([O:10][CH3:11])=[O:9])[C@H:5]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[C@@H:4]([C:26]([O:28][CH3:29])=[O:27])[CH2:3]1)([CH3:39])([CH3:38])[CH3:36]

Komponenten

5

Edukt 3

HCID 79177tert-Butyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 67304346dimethyl(2S,3S,5S)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Produkt 1

HCID 67303979Dimethyl (2s,3s,5s)-5-(2-tert-butoxy-2-oxoethoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of dimethyl (2S,3S,5S)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate (50.0 mg, 0.000123 mol) in tetrahydrofuran (0.50 mL, 0.0062 mol) was added 1.00 M of potassium tert-butoxide in tetrahydrofuran (0.150 mL). After stirred at rt for 30 min, to the mixture was added bromo-acetic acid 1,1-dimethylethyl ester (0.0228 mL, 0.000154 mol). The resulting mixture was stirred at rt overnight and then concentrated to dry.

Aufarbeitung

  1. stirringThe resulting mixture was stirred at rt overnight
  2. concentrationconcentrated
  3. customto dry

Quellen und Nachweise

ORD-Eintrag
ord-f1678fb6229b4bf6b96a8df698f5cc52
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853243B2

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