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Dichloromethane → dimethyl(2S,3S,5S)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

HRID 535086
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 535086
[C:1]([O:5][C@@H:6]1[CH2:11][NH:10][C@H:9]([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:8]([C:26]([O:28][CH3:29])=[O:27])[CH2:7]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.Cl[C:34]([O:36][CH3:37])=[O:35]>CN(C)C1C=CN=CC=1>[C:1]([O:5][C@@H:6]1[CH2:11][N:10]([C:34]([O:36][CH3:37])=[O:35])[C@H:9]([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:8]([C:26]([O:28][CH3:29])=[O:27])[CH2:7]1)([CH3:4])([CH3:3])[CH3:2]
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Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 67304371Methyl (2s,3s,5s)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate

Produkt 1

HCID 67304316dimethyl(2S,3S,5S)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14284
4-(Dimethylamino)pyridine
Katalysator

Versuchsvorschrift

To a mixture of methyl (2S,3S,5S)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate (0.03345 g, 8.290E-5 mol) and 4-dimethylaminopyridine (0.0152 g, 0.000124 mol) in methylene chloride (1.50 mL, 0.0234 mol) was added methyl chloroformate (0.00833 mL, 0.000108 mol). The reaction was stirred at rt overnight. After quenched with aq. sodium bicaronate, the reaction was extracted with ethyl acetate. The combined organic layers were washed with brine, dried, concentrated to dry. The resulting residue was used directly in next step. MS (ESI): (M+H)+=462.2.

Aufarbeitung

  1. customAfter quenched with aq. sodium bicaronate
  2. extractionthe reaction was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto dry

Quellen und Nachweise

ORD-Eintrag
ord-dfa84b48f67745f59631001b7b7a1b56
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08853243B2

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