Aluminium lithium hydride → HCID 68593921, compound

HRID 517866Notes

Reaction equation

HRID 517866 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]([CH2:17][C:18](OCC)=[O:19])[C:12]3[CH2:23][CH2:24][N:25]([CH3:27])[CH2:26][C:11]=3[C:10]=2[CH:9]=1>C1COCC1>[Cl:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]([CH2:17][CH2:18][OH:19])[C:12]3[CH2:23][CH2:24][N:25]([CH3:27])[CH2:26][C:11]=3[C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 44159218Ethyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate

Product 1

HCID 68593921HCID 68593921, compoundYield 1.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of lithium aluminum hydride (0.059 g, 1.5 mmol) in THF (30 mL) was added ethyl 2-(8-chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)acetate (0.4 g, 1.3 mmol) in THF (10 mL) drop wise at 0° C. The reaction mixture was further heated at 100° C. for 6 h. Reaction was monitored by TLC and LCMS. On completion of the reaction, reaction mixture was quenched with H2O:NaOH:H2O (1:1:3) and the contents were filtered. The filtrate obtained was extracted with Ethyl acetate. Combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to obtain crude product (300 mg). 100 mg of the crude was purified by preparative TLC to obtain 5 mg of 2-(8-chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)ethanol as free base. The free base (0.015 g 0.056 mmol) was further dissolved in THF (2 mL), oxalic acid (0.007 g, 0.056 mmol) in THF (1 mL) was added to it and the resulting mixture was further stirred for 30 min at room temperature. The precipitate obtained was filtered and dried under vacuum to afford 20 mg of 2-(8-chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)ethanol as an oxalate salt. 1H NMR (CD3OD) 7.45 (s, 1H), 7.4 (d, 1H), 7.1 (d, 1H), 4.3 (s, 2H), 4.2 (t, 2H), 3.9 (t, 2H), 3.5 (t, 2H), 3.2 (t, 2H), 2.9 (s, 3H).

Workup

  1. customReaction
  2. customOn completion of the reaction, reaction mixture
  3. customwas quenched with H2O:NaOH:H2O (1:1:3)
  4. filtrationthe contents were filtered
  5. customThe filtrate obtained
  6. extractionwas extracted with Ethyl acetate
  7. dry with materialCombined organic layers were dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain crude product (300 mg)
  10. custom100 mg of the crude was purified by preparative TLC

Sources & evidence

ORD record
ord-a986b7233d044f29b68c85d9ed200aac
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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