Lithium borohydride → (R)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinemethanol

HRID 1450741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1450741
C[O:2][C:3]([C@@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=O.[BH4-].[Li+]>CCOCC>[CH3:11][C:7]1([CH3:10])[N:6]([C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C@H:5]([CH2:3][OH:2])[CH2:9][O:8]1

Komponenten

4

Edukt 2

HCID 4148881Lithium borohydrideHCID 53934458(S)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinecarboxylic Acid Methyl Ester

Produkt 1

HCID 54137581(R)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinemethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 8a (296 mg, 1.09 mmol) in dry ether (1 mL) is treated with lithium borohydride (2M solution in THF, 0.55 mL, 1.09 meq) under an argon atmosphere. The mixture is stirred for 3 h at reflux and 18 h at room temperature. The resulting mixture is diluted with ether and quenched with methanol. The volatiles are removed and the residue is taken up in EtOAc/H2O. Workup provides the crude alcohol which is purified by chromatography (2:1 hexane/EtOAc): NMR δ0.88 (m, 3H), 1.30 (m, 6H), 1.54 (s, 3H), 1.62 (s, 3H), 2.35 (m, 2H), 3.30-4.40 (complex m, 6H); MS (HR-E1) m/z 243.1837 (M calcd. for C13H25NO3 243.1840); [α]D26 =-5±1 (CHCl3).

Aufarbeitung

  1. customquenched with methanol
  2. customThe volatiles are removed

Quellen und Nachweise

ORD-Eintrag
ord-66daa9755dae42ffaefc422a20dd1a7a
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602275

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