o-Toluenesulfonyl chloride → 1-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidine

HRID 238087

Reaktionsgleichung

Reaktionsgleichung von HRID 238087
N12[CH2:8][CH2:7]N(CC1)CC2.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][OH:23])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].[C:24]1(C)[C:25]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:27]=C[CH:29]=1>COC(C)(C)C.CCOCC>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][O:23][S:30]([C:25]2[CH:26]=[CH:27][C:7]([CH3:8])=[CH:29][CH:24]=2)(=[O:32])=[O:31])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Komponenten

6

Edukt 3

HCID 8623o-Toluenesulfonyl chlorideHCID 9237DabcoHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Produkt 1

HCID 106428511-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidineAusbeute 62.906,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

1,4-Diazabicyclo[2.2.2]octane (42.4 g, 0.378 mol) was added to a solution of 1-(tert-butoxycarbonyl)-4-hydroxymethylpiperidine (52.5 g, 0.244 mol) in tert-butyl methyl ether (525 ml). After stiffing for 15 minutes at ambient temperature, the mixture was cooled to 5° C. and a solution of toluene sulphonyl chloride (62.8 g, 0.33 mmol) in tert-butyl methyl ether (525 ml) was added in portions over 2 hours while maintaining the temperature at 0° C. After stirring for 1 hour at ambient temperature, petroleum ether (1 l) was added. The precipitate was removed by filtration. The filtrate was evaporated to give a solid. The solid was dissolved in ether and washed successively with 0.5N aqueous hydrochloric acid (2×500 ml), water, saturated sodium hydrogen carbonate and brine, dried (MgSO4) and evaporated to give 1-(tert-butoxycarbonyl)-4-(4-methylphenylsulphonyloxymethyl)piperidine (76.7 g, 85%).

Aufarbeitung

  1. temperaturewhile maintaining the temperature at 0° C
  2. customThe precipitate was removed by filtration
  3. customThe filtrate was evaporated
  4. customto give a solid
  5. washwashed successively with 0.5N aqueous hydrochloric acid (2×500 ml), water, saturated sodium hydrogen carbonate and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ca9cbe1d6d034a839a21db8ac3b4945c
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642608B2

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