Tetrahydrofuran → 4-(2-Fluoropropan-2-yl)oxazolidin-2-one

HRID 57371Notes

Reaction equation

HRID 57371 reaction equation
[NH2:1][CH:2]([C:5]([F:8])([CH3:7])[CH3:6])[CH2:3][OH:4].C1C[O:12][CH2:11]C1>C(Cl)Cl>[F:8][C:5]([CH:2]1[CH2:3][O:4][C:11](=[O:12])[NH:1]1)([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 155336822-Amino-3-fluoro-3-methylbutan-1-ol

Product 1

HCID 904144754-(2-Fluoropropan-2-yl)oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N′-carbonyldiimidazole (530 mg, 3.27 mmol in THF (5 mL) was added slowly a solution of 2-amino-3-fluoro-3-methylbutan-1-ol (360 mg, 2.97 mmol) in THF (10 mL). The reaction mixture was stirred at room temperature for 18 hr, was diluted with DCM and stirred for additional 30 min. The separated organic layer was washed with water and brine, dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 12 g, EtOAc/heptane=0/100 to 80/20] to provide 4-(2-fluoropropan-2-yl)oxazolidin-2-one (150 mg) as a brown solid. MS m/z 148.0 (M+H)+; Rt-0.32 min. 1H NMR (400 Mhz, CDCl3) δ ppm 6.30 (br. s., 1H), 4.39-4.54 (m, 1H), 4.26 (dd, J=8.9, 5.1 Hz, 1H), 3.84-3.99 (m, 1H), 1.29-1.45 (m, 6H).

Workup

  1. stirringstirred for additional 30 min
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography [SiO2, 12 g, EtOAc/heptane=0/100 to 80/20]

Sources & evidence

ORD record
ord-7b216eb743fa445da00aaa739cb62177
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

Loading…