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

HRID 1009249Notes

Reaction equation

HRID 1009249 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-cc13fbe8013b439d9b49cec9ee72cfec
Source dataset
uspto-grants-2011_07
Patent number
US07973037B2

Reaction notes

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