Water → HCID 57515780, compound

HRID 1620952Notes

Reaction equation

HRID 1620952 reaction equation
Cl.[NH2:2][C@H:3]([CH2:7][OH:8])[CH2:4][CH2:5][CH3:6].CO[CH:11](O)[C:12]([F:15])([F:14])[F:13].C(N(CC)CC)C.O>C1C=CC=CC=1.CCOCC>[CH2:4]([C@H:3]1[CH2:7][O:8][CH:11]([C:12]([F:15])([F:14])[F:13])[NH:2]1)[CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 98922,2,2-Trifluoro-1-methoxyethanolHCID 74889769HCID 74889769, compound

Product 1

HCID 57515780HCID 57515780, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

(L)-Norvalinol hydrochloride (5.25 g, 37.60 mmol) and trifluoroacetaldehyde methyl hemiacetal (5 mL, 37.6 mmol) were heated in benzene (100 mL) in the presence of triethylamine (5.26 mL, 37.6 mmol) at reflux, using a Dean-Stark apparatus to trap water. After 3 hours, the reaction mixture was cooled, diluted with ether (100 mL), filtered, and evaporated to dryness, giving (4S)-4-propyl-2-trifluoromethyloxazolidine, which was used without further purification.

Workup

  1. temperatureat reflux
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-50032139534a41ed9ced72752a99f13b
Source dataset
uspto-grants-2014_07
Patent number
US08772336B2

Reaction notes

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