Aluminium lithium hydride → HCID 68761380, compound

HRID 529129Notes

Reaction equation

HRID 529129 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]2([C:20]3[C:19]([C:21]#[N:22])=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:13]2=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[CH2:21][NH2:22])[N:14]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69809227HCID 69809227, compound

Product 1

HCID 68761380HCID 68761380, compoundYield 17.1%

Procedure

A solution of 1′-benzyl-1-(4-methoxybenzyl)-2-oxospiro[indoline-3,3′-pyrrolidine]-4-carbonitrile (3.00 g, 7.08 mmol) in LAH (1.0M in THF, 35.4 mL, 35.4 mmol) was heated at reflux for 12 hours. The reaction mixture was quenched with Na2SO4-10 H2O, dried and filtered. The filter cake was washed with ethyl acetate, and the filtrate was concentrated. The residue was purified by chromatography (hexanes/ethyl acetate gradient) to give (1′-benzyl-1-(4-methoxybenzyl)spiro[indoline-3,3′-pyrrolidine]-4-yl)methanamine (500 mg, 1.21 mmol, 17%). LCMS (APCI+) M+H+ 414 (100%); Rt=3.23 min.

Workup

  1. temperatureat reflux for 12 hours
  2. customThe reaction mixture was quenched with Na2SO4-10 H2O
  3. customdried
  4. filtrationfiltered
  5. washThe filter cake was washed with ethyl acetate
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by chromatography (hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-78fa19004f5044818cc4622155807467
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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