2,2-Dimethoxypropane → tert-butyl (4S)-4-(2-methoxy-2-oxo-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylate

HRID 1254362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1254362
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][OH:16])[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[C:19](OC)([CH3:21])[CH3:20]>CC(C)=O.B(F)(F)F.CCOCC>[CH3:14][O:13][C:11](=[O:12])[CH2:10][C@H:9]1[CH2:15][O:16][C:19]([CH3:21])([CH3:20])[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7]

Komponenten

5

Edukt 2

HCID 64952,2-DimethoxypropaneHCID 54573797Methyl (S)-3-(Boc-amino)-4-hydroxybutanoate

Produkt 1

HCID 10923729tert-butyl (4S)-4-(2-methoxy-2-oxo-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8000Boron trifluoride etherateKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of (S)-methyl 3-(tert-butoxycarbonylamino)-4-hydroxybutanoate (7.0 g, 30.0 mmol) in acetone (90 mL), there was added 2,2-dimethoxypropane (37 mL, 300 mmol) followed by BF3.Et2O (0.11 mL, 0.9 mmol). The resulting solution was stirred at rt overnight. Solvents were removed under vacuum, and the residue was redissolved in ether (100 mL), washed with sat'd NaHCO3 (20 mL). Upon concentrating under vacuum, the residue was purified by flash column chromatography to give (S)-tert-butyl 4-(2-methoxy-2-oxoethyl)-2,2-dimethyloxazolidine-3-carboxylate (7.51 g, 92%). MS m/z 296 (M+Na+).

Aufarbeitung

  1. customSolvents were removed under vacuum
  2. dissolutionthe residue was redissolved in ether (100 mL)
  3. washwashed with sat'd NaHCO3 (20 mL)
  4. concentrationUpon concentrating under vacuum
  5. customthe residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6316ef4bf1f34b8c8565447ccd5f4e21
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455521B2

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