(Diethylamino)sulfur trifluoride → tert-butyl (4R)-4-(1-fluoro-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 1035501Notes

Reaction equation

O[C:2]([C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([CH3:4])[CH3:3].C(N(S(F)(F)[F:25])CC)C>C(Cl)Cl>[F:25][C:2]([C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

tert-Butyl (4R)-4-(1-hydroxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (3.80 g, 14.7 mmol), prepared by the method of Joullie, Tetrahedron, 52, pp. 11673-11694, (1996) was dissolved in 90 mL of anhydrous CH2Cl2. The solution was cooled to −78° C. under an atmosphere of N2. (Diethylamino)sulfur trifluoride (DAST) (2.25 mL, 17.0 mmol) was added and the reaction was allowed to warm to ambient temperature overnight. The reaction was quenched with saturated NaHCO3 solution and the layers were separated. The organic portion was washed successively with H2O and brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography (SiO2, 7% EtOAc/hexanes) gave tert-butyl (4R)-4-(1-fluoro-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1.98 g) as a nearly colorless liquid.

Workup

temperatureto warm to ambient temperature overnight
customThe reaction was quenched with saturated NaHCO3 solution
customthe layers were separated
washThe organic portion was washed successively with H2O and brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-1d6f9e6c3f7e4fa3bdc70bf112edc5f3
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546383B2

Reaction notes

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