Water → (r)-5-Tert-butyl-3-((tetrahydrofuran-2-yl)methyl)oxazol-2(3h)-imine

HRID 536716Notes

Reaction equation

HRID 536716 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][NH:7][C:8]#[N:9].Br[CH2:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CC(=O)CC>[C:13]([C:12]1[O:17][C:8](=[NH:9])[N:7]([CH2:6][C@H:2]2[CH2:3][CH2:4][CH2:5][O:1]2)[CH:11]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 55288151(R)-tetrahydrofuran-2-ylmethyl-cyanamide

Product 1

HCID 66643286(r)-5-Tert-butyl-3-((tetrahydrofuran-2-yl)methyl)oxazol-2(3h)-imine

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of Example 32A (2.35 g, 18.63 mmol), 1-bromo-3,3-dimethylbutan-2-one (2.52 mL, 18.63 mmol) and potassium carbonate (2.57 g, 18.63 mmol) in 2-butanone (75 mL) was heated to 80° C. overnight. The mixture was poured into water, and extracted with ethyl acetate (2×). The combined organic extracts were dried over Na2SO4, filtered, concentrated under reduced pressure to afford the title compound. MS (ESI) m/z 225 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-497d45d273f247efa75371f14397e937
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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