Ethyl 9-ethyl-9H-beta-carboline-3-carboxylate → HCID 58443257, compound

HRID 1630753Notes

Reaction equation

HRID 1630753 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[N:13]=[CH:14][C:15]2[N:16]([CH2:25][CH3:26])[C:17]3[C:22]([C:23]=2[CH:24]=1)=[CH:21][CH:20]=[CH:19][CH:18]=3)=O)C>O1CCCC1>[CH2:25]([N:16]1[C:15]2[CH:14]=[N:13][C:12]([CH:10]=[O:9])=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:26]

Participants

4

Reactant 2

HCID 14221744Ethyl 9-ethyl-9H-beta-carboline-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 58443257HCID 58443257, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of lithium aluminium hydride (116 mg, 3.06 mmol, 1 eq) in anhydrous tetrahydrofuran (15 mL) was added at 0° C. under nitrogen a solution of 9-ethyl-9H-β-carboline-3-carboxylic acid ethyl ester (820 mg, 3.06 mmol, 1 eq) in anhydrous tetrahydrofuran (25 mL). The reaction mixture was stirred at 0° C. for 6 h then quenched with a 5% aqueous solution of sodium hydroxide (2.88 mL). The solid formed was filtered, washed with ethyl acetate and dried to afford the title compound, which is used without further purification. Mass Spec m/z=227 [M+H+].

Workup

  1. customthen quenched with a 5% aqueous solution of sodium hydroxide (2.88 mL)
  2. customThe solid formed
  3. filtrationwas filtered
  4. washwashed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-57abc12dd3ab4497b329d3725f20724e
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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