Triethylamine → Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

HRID 15519

Reaktionsgleichung

Reaktionsgleichung von HRID 15519
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.CCN(CC)CC.[CH3:23][S:24](Cl)(=[O:26])=[O:25].CCOC(C)=O>C1COCC1.O>[CH3:23][S:24]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)(=[O:26])=[O:25]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Produkt 1

HCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylateAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (Aldrich) (4.30 g, 20 mmol) and Et3N (5 mL) in THF (60 mL) at 0° C. was added MeSO2Cl (1.6 mL) dropwise with stirring. After 2.5 h EtOAc (160 mL) and water (50 mL) were added to the reaction mixture, the EtOAc layer was separated, washed with 1N HCl (30 mL), dried over MgSO4, concentrated in vacuo to obtain the product (5.8 g, 98.9%) as a low melting white solid. This material was used directly for the next step without any further purification. 1H NMR (CDCl3) δ 4.20 (m, 2H), 4.04 (d, 2H, J=6.1 Hz), 2.99 (s, 3H), 2.68 (m, 2H), 2.01-1.70 (m, 3H), 1.43 (s, 9H), 1.20 (m, 2H).

Aufarbeitung

  1. customthe EtOAc layer was separated
  2. washwashed with 1N HCl (30 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6a1b5ad903a543eab3bf4a269d1eb3a3
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732613B2

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