Aluminium lithium hydride → HCID 66972054, compound

HRID 1364207Notes

Reaction equation

HRID 1364207 reaction equation
[F:1][C:2]([F:37])([F:36])[CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C@@H:6]([NH:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[F:37][C:2]([F:1])([F:36])[CH2:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C@@H:6]([NH:15][C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:5]1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66971860HCID 66971860, compound

Product 1

HCID 66972054HCID 66972054, compound

Conditions

Temperature
0 °C

Procedure

A round-bottom flask containing the product of Step 1 (1.94 g, 3.88 mmol) was fitted with a condenser, stirbar and septa and flushed with nitrogen. Tetrahydrofuran (40 mL) was added, giving a solution that was cooled to 0° C. Lithium aluminum hydride (0.77 g, 20 mmol) was added, and the reaction was then removed from the cooling bath and allowed to warm to room temperature. After one hour, the reaction was warmed to 60° C., then stirred an additional 17 hours. The reaction mixture was then cooled to room temperature and quenched via the sequential additions of H2O (0.77 mL), 10% aqueous sodium hydroxide solution (0.77 mL), and H2O (3×0.77 mL). The resulting mixture was stirred 10 minutes, diluted with ethyl acetate (100 mL), filtered through celite and concentrated in vacuo to give the desired product.

Workup

  1. customwas fitted with a condenser
  2. customstirbar and septa and flushed with nitrogen
  3. additionTetrahydrofuran (40 mL) was added
  4. customgiving a solution that
  5. customthe reaction was then removed from the cooling bath
  6. temperatureto warm to room temperature
  7. temperaturethe reaction was warmed to 60° C.
  8. temperatureThe reaction mixture was then cooled to room temperature
  9. customquenched via the sequential additions of H2O (0.77 mL), 10% aqueous sodium hydroxide solution (0.77 mL), and H2O (3×0.77 mL)
  10. stirringThe resulting mixture was stirred 10 minutes
  11. additiondiluted with ethyl acetate (100 mL)
  12. filtrationfiltered through celite and
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55c7598666254caaa903e29cd2fa167b
Source dataset
uspto-grants-2011_02
Patent number
US07888345B2

Reaction notes

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