StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Water → (S)-benzyl 3-(tert-butoxycarbonyl(ethyl)amino)piperidine-1-carboxylate

HRID 919579
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 919579
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:27](Br)[CH3:28].O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH2:27][CH3:28])[C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 50999241(S)-1-Cbz-3-Boc-Aminopiperidine

Produkt 1

HCID 68070545(S)-benzyl 3-(tert-butoxycarbonyl(ethyl)amino)piperidine-1-carboxylateAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of (S)-benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate (500 mg, 1.49 mmol) in DMF (5 mL) was added NaH (60% suspension in mineral oil, 120 mg, 1.64 mmol) and the reaction mixture was stirred for 1 h. To the reaction mixture was added ethyl bromide (0.12 mL, 1.64 mmol) and the reaction mixture was stirred for 4 h. The reaction mixture was diluted with ice-cooled water and the solution was extracted with EtOAc, the EtOAc layer was dried over Na2SO4 and concentrated in vacuo to give the crude product that was purified by column chromatography (silica gel, gradient, EtOAc in hexanes) to give (300 mg, 55%) of the titled compound. 1H NMR (400 MHz, CDCl3): δ 7.36-7.30 (m, 5H), 5.18-5.12 (m, 2H), 4.18-4.13 (m, 2H), 3.68-3.62 (m, 1H), 3.22-3.17 (m, 2H), 3.01-2.85 (m, 1H), 2.68-2.59 (m, 1H), 1.89-1.81 (m, 1H), 1.78-1.73 (m, 2H), 1.55 (s, 9H), 1.54-1.48 (m, 1H), 1.08 (t, J=6.4 Hz, 3H). ES-MS: m/z [M+1]=363.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 4 h
  2. additionThe reaction mixture was diluted with ice-
  3. extractionthe solution was extracted with EtOAc
  4. dry with materialthe EtOAc layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product that
  7. customwas purified by column chromatography (silica gel, gradient, EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-39b3cf7c121b4431ac0bab30f976f8fe
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09273028B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion