Triethylamine → (S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate

HRID 522628

Reaktionsgleichung

[OH:1][CH2:2][C@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.C(N(CC)CC)C.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>ClCCl>[CH3:26][S:23]([O:1][CH2:2][C@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)(=[O:25])=[O:24]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of (S)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (3.0 g, 13.8 mmol) and triethylamine (4.2 g, 41.4 mmol) in dichloromethane (80 mL) at 0° C. was dropwise added mesyl chloride (1.9 g, 16.5 mmol). The reaction mixture was stirred at 0° C. for 2 hour, and then diluted with dichloromethane (100 mL). The organic layers were washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford (S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate as a purple oil (4.0 g, 98%), which was directly used in the next step without further purification. MS (ES+) C11H21NO6S requires: 295, found: 240 [M+H-56]+.

Aufarbeitung

customat 0° C.
washThe organic layers were washed with water (100 mL) and brine (100 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-d8089c48fc6c46bfad3a755251fe9aa4
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09334263B2

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