Trityl chloride → Tert-butyl 4-[3-(tert-butoxy)-2-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate

HRID 47324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47324
[OH:1][CH:2]([CH2:18][OH:19])[CH2:3][C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.Cl[C:21]([C:34]1C=CC=CC=1)([C:28]1C=CC=CC=1)[C:22]1C=CC=CC=1>N1C=CC=CC=1>[C:21]([O:19][CH2:18][CH:2]([OH:1])[CH2:3][C:4]1([OH:17])[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:8][CH2:9]1)([CH3:34])([CH3:28])[CH3:22]

Komponenten

4

Edukt 2

HCID 6456Trityl chlorideHCID 22744545Tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate

Produkt 1

HCID 22744586Tert-butyl 4-[3-(tert-butoxy)-2-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylateAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

9.11 g of tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate was dissolved in 40 ml pyridine, 10.0 g of chlorotriphenylmethane was added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was partitioned into ethyl acetate and water, washed with 2 N hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine, and dried over magnesium sulfate. After filtration, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 10.3 g of tert-butyl 4-[3-(tert-butoxy)-2-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate.

Aufarbeitung

  1. customThe reaction solution was partitioned into ethyl acetate and water
  2. washwashed with 2 N hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e9eadd2fa35b437b8d5d983f848468fb
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699870B2

Notizen zur Reaktion

Wird geladen…