Triethylamine → (2R)-1-Boc-2-(methanesulfonyloxymethyl)azetidine

HRID 902959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902959
[C:1]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][OH:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1COCC1>[C:1]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][O:13][S:22]([CH3:21])(=[O:24])=[O:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11074142(R)-1-Boc-2-azetidinemethanol

Produkt 1

HCID 11140030(2R)-1-Boc-2-(methanesulfonyloxymethyl)azetidineAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of (2R)-1-Boc-2-(hydroxymethyl)azetidine (1.5 g, 8.0 mmol; see Tetrahedron Asym. 1998, 9, 2791) and triethylamine (3.5 g, 35 mmol; Spectrum) in dry THF (20 mL) was cooled to 0° C., and methanesulfonyl chloride (0.75 mL, 9.7 mmol; Aldrich) was added slowly with stirring. The reaction mixture was allowed to warm to room temperature and stir for 1 hour, then the solid was removed by filtration and the organic phase was concentrated. The residue was dissolved in dichloromethane (40 mL), washed with water (20 mL), and then concentrated to afford the title compound (800 mg, 3.0 mmol; 38% yield). MS (DCl/NH3): 266 (M+1)+, 283 (M+18)+.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringstir for 1 hour
  3. customthe solid was removed by filtration
  4. concentrationthe organic phase was concentrated
  5. dissolutionThe residue was dissolved in dichloromethane (40 mL)
  6. washwashed with water (20 mL)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-573e49de07164d24b1d1b350ff1f1e5b
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365193B2

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