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

HRID 2223516Notes

Reaction equation

HRID 2223516 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-393c4c865409422b9ed6b81512bd9339
Source dataset
uspto-grants-2008_05
Patent number
US07375134B2

Reaction notes

Loading…