Tetrahydrofuran → (R)-tert-butyl 4-(3-hydroxypentan-3-yl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 627214

Reaction equation

HRID 627214 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[CH2:5]([Mg]Br)[CH3:6].[CH3:9][C:10]1([CH3:26])[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:13]([C:22]([O:24]C)=O)[CH2:12][O:11]1.[CH2:27]1COC[CH2:28]1>>[OH:24][C:22]([C@H:13]1[CH2:12][O:11][C:10]([CH3:9])([CH3:26])[N:14]1[C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])([CH2:5][CH3:6])[CH2:27][CH3:28]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24636Cerium(III) chlorideHCID 6882203-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 89851480(R)-tert-butyl 4-(3-hydroxypentan-3-yl)-2,2-dimethyloxazolidine-3-carboxylateYield 95%

Conditions

Temperature
-78 °C

Procedure

A suspension of cerium (III) chloride (119 g, 482.07 mmol) in THF (350 mL) at room temperature was stirred vigorously for 2 hours. The suspension was cooled to −78° C. and ethylmagnesium bromide (482 mL, 482.07 mmol) was added dropwise. The mixture was stirred at −78° C. for 1.5 hours. (R)-3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (Aldrich, 25 g, 96.41 mmol) in THF (100 mL) was then added dropwise at −78° C. The reaction was stirred at −78° C. for 30 minutes and then warmed to 0° C. for 15 minutes. The reaction was quenched with saturated NH4Cl, diluted further with water and extracted twice with ether. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the title compound (26.4 g, 95%) as a colorless oil.

Workup

  1. stirringThe mixture was stirred at −78° C. for 1.5 hours
  2. stirringThe reaction was stirred at −78° C. for 30 minutes
  3. temperaturewarmed to 0° C. for 15 minutes
  4. customThe reaction was quenched with saturated NH4Cl
  5. additiondiluted further with water
  6. extractionextracted twice with ether
  7. dry with materialThe organics were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8c7716b9b106400ca34f40fd57b9152c
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Linked notes

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