Water → cis-l-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine

HRID 344290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 344290
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH:10]([OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][O:15][S:25]([CH3:24])(=[O:27])=[O:26])[C@H:10]([OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][O:15][S:25]([CH3:24])(=[O:27])=[O:26])[C@H:10]([OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 154810601,1-Dimethylethyl 3-hydroxy-4-(hydroxymethyl)-1-piperidinecarboxylate

Produkt 2

HCID 86753635cis-l-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidineHCID 86753636trans-1-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-tert-butoxycarbonyl-3-hydroxy-4-hydroxymethylpiperidine (6.5 g) and triethylamine (5.87 ml) in dichloromethane (100 ml) was added dropwise methanesulfonyl chloride (3.54 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 6 hr. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=40:1) to give 4.44 g of cis-l-tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine and 0.93 g of trans-1-tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine.

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-cb436ae2cbc1490ba74c7a83af05b90a
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05864039

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