Aluminium lithium hydride → HCID 22707927, compound

HRID 353122Notes

Reaction equation

HRID 353122 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:25])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[O:24][CH:23]=[N:22][CH:21]=3)[CH:15]=2)[CH:10]([CH3:26])[CH2:9]1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:25])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[O:24][CH:23]=[N:22][CH:21]=3)[CH:15]=2)[CH:10]([CH3:26])[CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22707886HCID 22707886, compound

Product 1

HCID 22707927HCID 22707927, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-hexanoyl-3,4-dimethyl-4-(3-(1,3-oxazol-5-yl)phenyl)piperidine (Preparation 36, 292 mg, 0.83 mmol) in tetrahydrofuran (6.0 mL) at 0° C. was added lithium aluminium hydride (1.0 M solution in tetrahydrofuran, 0.80 mL, 0.80 mmol) dropwise over a few minutes. The solution was stirred at room temperature under a nitrogen atmosphere for 30 minutes and then heated at reflux for 30 minutes before it was cooled back to 0° C. The reaction was cautiously quenched by the addition of 1 N sodium hydroxide (1.0 mL) and then ethyl acetate (excess) and solid sodium hydrogencarbonate (excess) were added. The mixture was stirred vigorously for 1 h and then filtered through Celite®, washing with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with ethyl acetate:hexane:ammonia (90:10:1). The title compound was isolated as clear oil (233 mg, 83%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 minutes before it
  3. temperaturewas cooled back to 0° C
  4. customThe reaction was cautiously quenched by the addition of 1 N sodium hydroxide (1.0 mL)
  5. additionethyl acetate (excess) and solid sodium hydrogencarbonate (excess) were added
  6. stirringThe mixture was stirred vigorously for 1 h
  7. filtrationfiltered through Celite®
  8. washwashing with ethyl acetate
  9. concentrationThe filtrate was concentrated in vacuo
  10. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate:hexane:ammonia (90:10:1)

Sources & evidence

ORD record
ord-7b488976a7394335a340c0a825610d47
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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