Aluminium lithium hydride → HCID 68737579, compound

HRID 529105Notes

Reaction equation

HRID 529105 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:20]([C:22]#[N:23])=[CH:19][CH:18]=[CH:17][C:16]=3[NH:15][C:14]2=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH2:22][NH2:23])[NH:15][CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68737330HCID 68737330, compound

Product 1

HCID 68737579HCID 68737579, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1′-benzyl-2-oxospiro[indoline-3,4′-piperidine]-4-carbonitrile (0.88 g, 2.8 mmol) in THF (20 mL) was added dropwise a solution of 1N LiAlH4 in THF (11 mL, 11 mmol) at about 0° C. under N2. The reaction mixture was allowed to warm to about room temperature and stirred overnight. The reaction was then heated at reflux for 1 h. After cooling, the reaction was quenched by the dropwise addition of water (0.44 mL), followed by 3N NaOH (0.44 mL) and water (1.3 mL) at about 0° C. The mixture was diluted with Ether and stirred for about 10 min. The reaction mixture was filtered through Celite. The filtrate was concentrated to give crude (1′-benzylspiro[indoline-3,4′-piperidine]-4-yl)methanamine, which was carried forward in the next step without further purification. LCMS (APCI+) m/z 308 [M+H]+; Rt=1.96 min.

Workup

  1. temperatureto warm to about room temperature
  2. temperatureThe reaction was then heated
  3. temperatureat reflux for 1 h
  4. temperatureAfter cooling
  5. customthe reaction was quenched by the dropwise addition of water (0.44 mL)
  6. customfollowed by 3N NaOH (0.44 mL) and water (1.3 mL) at about 0° C
  7. additionThe mixture was diluted with Ether
  8. stirringstirred for about 10 min
  9. filtrationThe reaction mixture was filtered through Celite
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-270f2107ca8840bd919dcf7fffa00f7a
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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