Aluminium lithium hydride → HCID 68593399, compound

HRID 517867Notes

Reaction equation

HRID 517867 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[CH2:25][CH2:24][C:11]2[N:12]([CH2:20][C:21](O)=[O:22])[C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][C:18]=3[C:10]=2[CH2:9]1>C1COCC1>[CH3:7][N:8]1[CH2:25][CH2:24][C:11]2[N:12]([CH2:20][CH2:21][OH:22])[C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][C:18]=3[C:10]=2[CH2:9]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 591616282-(1,2,3,4-Tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetic acid

Product 1

HCID 68593399HCID 68593399, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium Aluminum Hydride (0.088 g, 2.3 mmol) was charged in dry THF (5 mL) and the contents cooled to 0° C. 2-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)acetic acid (0.2 g, 0.77 mmol) was then added to it portion wise. The reaction mixture was refluxed overnight. The reaction mixture was cooled to 0° C. and quenched with aqueous sodium sulfate. The solid formed was filtered through Celite, washed with THF, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product, which was then purified by column chromatography to give 2-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)ethanol. 10 mg of it was taken in dry THF (2 mL), oxalic acid (5 mg) was added to it. The solvent was evaporated under reduced pressure to afford 0.1 g of 2-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)ethanol as oxalate salt. 1H NMR (DMSO) 7.4 (d, 1H), 7.2 (s, 1H), 7.0 (d, 1H), 4.4 (bs, 1H), 4.2 (s, 2H), 3.7 (bs, 2H), 3.2 (bs, 2H), 2.9 (s, 3H), 2.6-2.4 (m, 4H), 2.3 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched with aqueous sodium sulfate
  4. customThe solid formed
  5. filtrationwas filtered through Celite
  6. washwashed with THF
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain the crude product, which
  10. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-b770ad6687cb4d6b8dda50224750ff24
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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