Dimethylformamide → (S)-1-[(S)-1-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)methyl]-3-methyl-piperidine-3-carboxylic acid ethyl ester

HRID 2366034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366034
[CH2:1]([O:3][C:4]([C@@:6]1([CH3:12])[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].[O:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:15][C@@H:14]1[CH2:23]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:1]([O:3][C:4]([C@@:6]1([CH3:12])[CH2:11][CH2:10][CH2:9][N:8]([CH2:23][C@@H:14]2[O:13][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[O:16][CH2:15]2)[CH2:7]1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 7101148(R)-(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl 4-methylbenzenesulfonateHCID 23389262(S)-Ethyl 3-methylpiperidine-3-carboxylate

Produkt 1

HCID 25176453(S)-1-[(S)-1-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)methyl]-3-methyl-piperidine-3-carboxylic acid ethyl esterAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of (S)-ethyl-3-methylpiperidine-3-carboxylate (7.23 g, 42.2 mmol), Toluene-4-sulfonic acid (R)-1-(2,3-dihydro-benzo[1,4]dioxin-2-yl)methyl ester (15.0 g, 44.3 mmol), potassium carbonate (6.42 g, 46.4 mmol) and N,N-dimethyl formamide (50 ml) was heated to 120° C. After 4 hours the reaction mixture was cooled down, water (35 ml) was added and the mixture was extracted twice with ethyl acetate. The combined ethyl acetate layers were evaporated to dryness. Toluene (35 ml) was added to the evaporation residue and the mixture was extracted twice with 1M HCl. The combined acidic water layers were made basic with aq NaOH. The basic water layer was extracted twice with ethyl acetate and the combined ethyl acetate layers were evaporated to dryness to yield 10.8 g (76%) of the title compound.

Aufarbeitung

  1. temperatureAfter 4 hours the reaction mixture was cooled down
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. customThe combined ethyl acetate layers were evaporated to dryness
  4. additionToluene (35 ml) was added to the evaporation residue
  5. extractionthe mixture was extracted twice with 1M HCl
  6. extractionThe basic water layer was extracted twice with ethyl acetate
  7. customthe combined ethyl acetate layers were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-96417703f9b1430ebfc80281f398aada
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697723B2

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