1-tert-Butyl 3-ethyl 1H-indole-1,3-dicarboxylate → 1-tert-Butyl 3-ethyl indoline-1,3-dicarboxylate

HRID 863298Notes

Reaction equation

HRID 863298 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 539833451-tert-Butyl 3-ethyl 1H-indole-1,3-dicarboxylate

Product 1

HCID 196977841-tert-Butyl 3-ethyl indoline-1,3-dicarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.0 g of ethyl 1-(tert-butoxycarbonyl)indole-3-carboxylate in 20 ml of anhydrous ethanol is hydrogenated in the presence of 0.50 g of palladium-on-charcoal (5% of Pd) at 80° C. until the reaction has ended. After the reaction mixture has been filtered over Celite '545 and the filtrate has been concentrated, the oily residue is purified by means of FC over 15 g of silica gel with a 15:1 mixture of hexane and ethyl acetate as the mobile phase. This gives the title compound: Rf (G)=0.39; anal. calc. for C16H21NO4 : C65.96%, H7.27%, N4.81%; found C65.67%, H7.18%, N4.77%.

Workup

  1. filtrationAfter the reaction mixture has been filtered over Celite '545
  2. concentrationthe filtrate has been concentrated
  3. customthe oily residue is purified by means of FC over 15 g of silica gel with a 15:1 mixture of hexane and ethyl acetate as the mobile phase

Sources & evidence

ORD record
ord-39ed7b3c3ad74147ae97dbe19d8e2b3d
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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