tert-butyl N-methyl-N-(3-oxopropyl)carbamate → HCID 68490529, Verbindung

HRID 1500341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500341
[CH3:1][N:2]([CH2:10][CH2:11][CH:12]=O)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Cl.Cl.[CH3:16][N:17]([CH3:29])[C:18]1([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(B)#N.[Na].CO.C(Cl)(Cl)Cl>CO.C(O)(=O)C>[CH3:16][N:17]([CH3:29])[C:18]1([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][N:21]([CH2:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH2:20][CH2:19]1

Komponenten

7

Edukt 4

HCID 10442454tert-butyl N-methyl-N-(3-oxopropyl)carbamateHCID 21584188Chloroform methanolHCID 67369868HCID 67369868, VerbindungHCID 101953985CID 101953985

Produkt 1

HCID 68490529HCID 68490529, VerbindungAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6.4 g (1.3 eq) tert-butyl methyl(3-oxopropyl)carbamate were added to a solution of 7.5 g (1 eq) N,N-dimethyl-4-(thiophen-2-yl)piperidin-4-amine bis hydrochloride in 75 ml methanol at 0° C. and the reaction mixture was stirred for 15 min at 0° C. 4.9 g (3 eq) sodium cyanoboron hydride were then added in portions and the mixture was stirred for 90 min at room temperature. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). As the conversion was not yet complete, the pH of the reaction mixture was adjusted to 5-6 with acetic acid and the mixture was stirred for 12 h at room temperature. Once the conversion was complete, the methanol was distilled off, water was added, the mixture obtained was extracted with IPA/chloroform (2×100 ml) and the combined organic phases were dried over Na2SO4. Following removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica gel; 5% MeOH/CHCl3). 8.5 g (84%) of product were obtained.

Aufarbeitung

  1. stirringthe mixture was stirred for 90 min at room temperature
  2. stirringthe mixture was stirred for 12 h at room temperature
  3. distillationthe methanol was distilled off
  4. additionwater was added
  5. customthe mixture obtained
  6. extractionwas extracted with IPA/chloroform (2×100 ml)
  7. dry with materialthe combined organic phases were dried over Na2SO4
  8. customremoval of the solvent under reduced pressure
  9. customthe residue was purified by column chromatography (silica gel; 5% MeOH/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-7980c59463764d378caaf4f9efea57e1
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206156B2

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