Aluminum(III) Chloride → HCID 178521074, compound

HRID 1960041Notes

Reaction equation

HRID 1960041 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:11]([O:18][CH2:19][CH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([C@@:27]23[CH2:34][CH2:33][C:32](=O)[N:31]2[C@@H:30]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:29][O:28]3)[CH2:23][CH2:22]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([O:18][CH2:19][CH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([C@H:27]2[CH2:34][CH2:33][CH2:32][N:31]2[C@@H:30]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:29][OH:28])[CH2:23][CH2:22]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 178515714HCID 178515714, compound

Product 1

HCID 178521074HCID 178521074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a cooled (0° C.) mixture of anhydrous AlCl3 (6.30 g, 47 mmol) in THF (300 mL) is slowly added lithium aluminum hydride (5.95 g, 157 mmol), and the resulting mixture is stirred at the same temperature for 10 min. To the resulting stirred and cooled (−65° C.) THF mixture is added trans-(3S,7aS)-7a-[4-(benzyloxyethyl)cyclohexyl]-3-phenyltetrahydropyrrolo[2,1-b]oxazol-5-one (22.0 g, 52 mmol) dissolved in THF (150 mL) over 30 min. The resulting mixture is stirred at the same temperature for 2 hours, and then warmed to room temperature and stirred additional 1 hour. The resulting mixture is cooled to 0° C., quenched by careful addition of Na2SO4-10H2O, and stirred for additional 30 min at room temperature. The insoluble matter is filtered and the filtrate is concentrated in vacuo to afford crude trans-(S)-2-{(R)-2-[4-(benzyloxyethyl)cyclohexyl]pyrrolidin-1-yl}-2-phenylethanol, which is used without further purification.

Workup

  1. temperatureTo a cooled
  2. stirringTo the resulting stirred
  3. stirringThe resulting mixture is stirred at the same temperature for 2 hours
  4. stirringstirred additional 1 hour
  5. temperatureThe resulting mixture is cooled to 0° C.
  6. customquenched by careful addition of Na2SO4-10H2O
  7. stirringstirred for additional 30 min at room temperature
  8. filtrationThe insoluble matter is filtered
  9. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-3ced2a2ba7e143e3a6b09669ca5cc0bf
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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