tert-butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylate → Ethyl 2-(1H-indol-2-yl)propanoate

HRID 1847829Notes

Reaction equation

HRID 1847829 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([C:7]1[N:8](C(OC(C)(C)C)=O)[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:6])[CH3:2]>ClCCl.C(O)(C(F)(F)F)=O>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:7]1[CH:5]([CH3:6])[C:4]([O:3][CH2:1][CH3:2])=[O:23]

Participants

4

Reactant 1

HCID 59129246tert-butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylate

Product 1

HCID 10921945Ethyl 2-(1H-indol-2-yl)propanoateYield 50%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 2-(1-ethoxy-1-oxopropan-2-yl)-1H-indole-1-carboxylate (2.77 g, 8.74 mmol) was dissolved in dichloromethane (25 mL) before TFA (9.8 mL) was added. The mixture was stirred for 1.5 h at room temperature. The mixture was evaporated to dryness, taken up in dichloromethane and washed with sat. aq. sodium bicarbonate, water, and brine. The product was purified by column chromatography on silica gel (0-20% EtOAc in hexane) to give ethyl 2-(1H-indol-2-yl)propanoate (0.92 g, 50%).

Workup

  1. additionwas added
  2. customThe mixture was evaporated to dryness
  3. washwashed with sat. aq. sodium bicarbonate, water, and brine
  4. customThe product was purified by column chromatography on silica gel (0-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-9d2b9a9362f54956972c2c49bc19d163
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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