1-Propanol, 2,2,3,3,3-pentafluoro-1-methoxy- → (4S)-4-isobutyl-2-(pentafluoroethyl)-1,3-oxazolidine

HRID 1620912Notes

Reaction equation

HRID 1620912 reaction equation
[CH3:1][O:2][CH:3](O)[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].[NH2:12][C@H:13](CO)[CH2:14][CH:15]([CH3:17])[CH3:16]>C1C=CC=CC=1>[CH2:14]([C@H:13]1[CH2:1][O:2][CH:3]([C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6])[NH:12]1)[CH:15]([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 1084041-Propanol, 2,2,3,3,3-pentafluoro-1-methoxy-HCID 111307L-Leucinol

Product 1

HCID 11413942(4S)-4-isobutyl-2-(pentafluoroethyl)-1,3-oxazolidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Pentafluoropropanal methyl hemiacetal (14.9 g, 82.8 mmol) and L-leucinol (9.7 g, 82.8 mmol) were dissolved in 100 mL of benzene and heated to reflux overnight in a flask equipped with a Dean-Stark tube. The resulting solution was cooled and concentrated to provide the title compound as an oil which was used directly in the following step.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight in a flask
  3. customequipped with a Dean-Stark tube
  4. temperatureThe resulting solution was cooled
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a506e9a982954c56bc8d8a7d0b612e19
Source dataset
uspto-grants-2014_07
Patent number
US08772336B2

Reaction notes

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