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

HRID 1880503Notes

Reaction equation

HRID 1880503 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-52023fe94ecb4d4e9d6624e75ae25b38
Source dataset
uspto-grants-2012_11
Patent number
US08318748B2

Reaction notes

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