alpha-Amino-7-ethyl-1H-indole-3-acetic Acid Ethyl Ester → HCID 14010222, compound

HRID 1788891Notes

Reaction equation

HRID 1788891 reaction equation
C([O:3][C:4](=O)[CH:5]([NH2:17])[C:6]1[C:14]2[C:9](=[C:10]([CH2:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:17][CH:5]([C:6]1[C:14]2[C:9](=[C:10]([CH2:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 14010221alpha-Amino-7-ethyl-1H-indole-3-acetic Acid Ethyl EsterHCID 21226445Aluminium lithium hydride

Product 1

HCID 14010222HCID 14010222, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

α-Amino-7-ethyl-1H-indole-3-acetic acid ethyl ester 6 (4.9 g, 0.02 mol) in THF (50 mL) was added to LiAlH4 (2.3 g, 0.06 mol) in THF (25 mL) and the mixture was refluxed for 2 hours to give β-amino-7-ethyl-1H-indole-3-ethanol 7 (3.5 g, 85.7%). A sample recrystallized from ethyl acetate-hexane had m.p. 84°-86° C.

Workup

  1. temperaturethe mixture was refluxed for 2 hours

Sources & evidence

ORD record
ord-5631154fce2f4da7b70e4f6954297de1
Source dataset
uspto-grants-1987_08
Patent number
US04686213

Reaction notes

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