Pyridine → N-BOC-3(R)-methylsulfonyloxymethyl-piperidine

HRID 1160345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160345
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N1C=CC=CC=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([CH2:14][O:15][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

Produkt 1

HCID 10108453N-BOC-3(R)-methylsulfonyloxymethyl-piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of N—BOC-3-piperidinemethanol (0.50 g, 0.002 mmole) in DCM (10 mL) was added dropwise pyridine (2.42 mL, 0.03 mmole) followed by the addition of methanesulfonyl chloride (0.774 mL, 0.01 mmole). The reaction mixture continued stirring at RT overnight. The reaction mixture was quenched with water. The aqueous layer was extracted with EtOAc (3×5 mL). Combined organic layers were dried over Na2SO4 and concentrated to yield a crude oil, 68, which was used in the next step without further purification. LRMS: 193 (M+-BOC group).

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionThe aqueous layer was extracted with EtOAc (3×5 mL)
  3. dry with materialCombined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customto yield a crude oil, 68, which
  6. customwas used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-a94c232791c6417ca5b9f80a4945474c
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816375B2

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