1-Phenethylamine, (-)- → (1S)-N-((R)-2,2-difluoro-hexahydro-5,5-dimethylindolizin-7(1H)-ylidene)-1-phenylethanamine

HRID 633350Notes

Reaction equation

HRID 633350 reaction equation
[F:1][C:2]1([F:14])[CH2:10][N:9]2[C@H:4]([CH2:5][C:6](=O)[CH2:7][C:8]2([CH3:12])[CH3:11])[CH2:3]1.[C:15]1([C@@H:21]([NH2:23])[CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[F:1][C:2]1([F:14])[CH2:10][N:9]2[C@H:4]([CH2:5][C:6](=[N:23][C@H:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH3:22])[CH2:7][C:8]2([CH3:12])[CH3:11])[CH2:3]1

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 86704459(R)-2,2-difluoro-hexahydro-5,5-dimethylindolizin-7(1H)-one

Product 1

HCID 86704461(1S)-N-((R)-2,2-difluoro-hexahydro-5,5-dimethylindolizin-7(1H)-ylidene)-1-phenylethanamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A toluene (12 ml) solution of (R)-2,2-difluoro-hexahydro-5,5-dimethylindolizin-7(1H)-one (487.8 mg, 2.4 mmol) and (S)-1-phenylethylamine (306 μL, 2.4 mmol) was heated under reflux in a flask equipped with a Dean-Stark distillation receiver. After 22 hours, most solvent was distilled off through Dean-Stark distillation receiver, and remaining solvent was removed in vacuo. Compound (1S)—N—((R)-2,2-difluoro-hexahydro-5,5-dimethylindolizin-7(1H)-ylidene)-1-phenylethanamine was obtained as a brown oil and was used directly in next reaction.

Workup

  1. temperatureunder reflux in a flask
  2. customequipped with a Dean-Stark distillation receiver
  3. distillationmost solvent was distilled off through Dean-Stark distillation receiver
  4. customwas removed in vacuo

Sources & evidence

ORD record
ord-3224709d4dd7469f901a4151e7767489
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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