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

HRID 1964383Notes

Reaction equation

HRID 1964383 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-143e0f35a3d04e7590af2046ddb58f1d
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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