tert-Butanol → HCID 18426153, Verbindung

HRID 1280983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280983
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH2:15][CH2:14][CH2:13][CH:9](C(O)=O)[CH2:8]2)=[CH:4][CH:3]=1.CC[N:20]([CH2:23]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.[CH3:42][C:43]([OH:46])([CH3:45])[CH3:44]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:15][CH2:14][CH2:13][CH:9]([NH:20][C:23]([O:46][C:43]([CH3:45])([CH3:44])[CH3:42])=[O:32])[CH2:8]2)=[CH:16][CH:17]=1

Komponenten

5

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 35450941-(4-chlorobenzyl)nipecotic acid

Produkt 1

HCID 18426153HCID 18426153, VerbindungAusbeute 32,6 %

Versuchsvorschrift

A solution of 1-(4-chlorobenzyl)nipecotic acid (7.06 g, 27.8 mmol) in tBuOH (500 mL) was treated with Et3N (3.38 g) and activated 3 A molecular sieves (30 g). Diphenylphosphoryl azide (8.58 g) was added, and the reaction mixture was warmed at reflux for 18 h. The mixture was cooled and the solvent was ref for 18 h. The mixture was cooled and the solvent was remove under vacuum. Tie residue was dissolved in EtOAc (500 mL), and the organic phase was washed with saturated aqueous NaHCO3 (2×100 mL) and brine (50 mL), dried (Na2SO4), and concentrated in vacuo. Chromatography (SiO2, 25% EtOAc-hexane) afforded 1-(4-chlorobenzyl)-3-{(tert-butoxycarbonyl)amino}piperidine (2.95 g, 32.6%) as a white crystalline solid: 1H NMR (CDCl3, 300 MHz) δ1.4-1.75 (br, 4 H), 2.2-2.7 (br, 4 H), 3.5 (br, 2 H), 3.8 (br, 1 H), 7.3 (br, 4 H); The purity was determined by RPLC/MS (>99%); ESI/MS m/e 269.2 (M++H−56, C17H26ClN2O2).

Aufarbeitung

  1. temperaturethe reaction mixture was warmed
  2. temperatureat reflux for 18 h
  3. temperatureThe mixture was cooled
  4. temperatureThe mixture was cooled
  5. customthe solvent was remove under vacuum
  6. dissolutionwas dissolved in EtOAc (500 mL)
  7. washthe organic phase was washed with saturated aqueous NaHCO3 (2×100 mL) and brine (50 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-27269e9ab98b400598d5de6be8f0d68c
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451842B1

Notizen zur Reaktion

Wird geladen…