Methanesulfonyl chloride → Tert-butyl 4-(3-((methylsulfonyl)oxy)propyl)piperidine-1-carboxylate

HRID 605798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605798
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)(=[O:4])=[O:3]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

Produkt 1

HCID 21190098Tert-butyl 4-(3-((methylsulfonyl)oxy)propyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methanesulfonyl chloride (2.7 ml) was dropwise added to a methylene chloride (200 ml) solution of tert-butyl 4-(3-hydroxypropyl)piperidine-1-carboxylate (8.00 g) and TEA (4.8 ml) at 0° C., followed by stirring overnight at room temperature. The reaction liquid was washed with aqueous saturated sodium hydrogencarbonate solution and saturated brine, then dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent: EtOAc:hexane=1:3 (v/v)) to obtain tert-butyl 4-{3-[(methylsulfonyl)oxy]propyl}piperidine-1-carboxylate (10.1 g).

Aufarbeitung

  1. customThe reaction liquid
  2. washwas washed with aqueous saturated sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (eluent: EtOAc:hexane=1:3 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-d99f58cd1de949e5861a4a8a5f2c9433
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915261B2

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