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

Acetic Acid → 1-(tert-Butyloxycarbonyl)-4-[4-chloro-(2-hydroxymethylphenylamino)] Piperidine

HRID 1823717
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1823717
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:17]=1[CH2:18][OH:19].C(O)(=O)C.[BH3-]C#N.[Na+]>C1(C)C=CC=CC=1.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:15][C:16]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:17]=2[CH2:18][OH:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic Acid2×HCID 5867542-Amino-5-chlorobenzyl alcoholHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 112100051-(tert-Butyloxycarbonyl)-4-[4-chloro-(2-hydroxymethylphenylamino)] Piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140
Toluene
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-(tert-butyloxycarbonyl)-4-piperidinone (20 g, 0.10 mol), 2-amino-5-chlorobenzyl alcohol (17.34 g, 0.11 mol) and acetic acid (14 mL, 0.22 mol) in dry toluene (500 mL) was heated at reflux temperature, with water elimination by means of azeotrope distillation with a Dean-Stark device, for 6 hours. The mixture was then cooled and vacuum concentrated up to half volume. NaBH3CN (20 g, 0.32 mol) and dry THF (300 mL) were added to the resulting solution. Acetic acid (10 mL, 0.17 mol) was then dripped for one hour. The reaction was stirred at room temperature for 24 hours. The mixture was vacuum concentrated and the residue was dissolved in ethyl acetate (750 mL), washed with a NaHCO3-saturated solution (4×250 mL) and a NaCl-saturated solution (250 mL), dried and evaporated to dryness. The residue was purified by means of flash chromatography eluting with a mixture of ethyl acetate:petroleum ether (1:3). The desired product was thus obtained as an oil (32.7 g, 96%).

Aufarbeitung

  1. temperatureat reflux temperature
  2. distillationwith water elimination by means of azeotrope distillation with a Dean-Stark device
  3. temperatureThe mixture was then cooled
  4. concentrationvacuum concentrated up to half volume
  5. concentrationconcentrated
  6. dissolutionthe residue was dissolved in ethyl acetate (750 mL)
  7. washwashed with a NaHCO3-saturated solution (4×250 mL)
  8. dry with materiala NaCl-saturated solution (250 mL), dried
  9. customevaporated to dryness
  10. customThe residue was purified by means of flash chromatography
  11. washeluting with a mixture of ethyl acetate:petroleum ether (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-2137e70662834151a281d15de0bb0a88
Quelldatensatz
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07041665B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion