Ethyl 5-methoxyindole-2-carboxylate → (RS)-5-methoxy-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester

HRID 1249932Notes

Reaction equation

HRID 1249932 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[CH:10][CH:9]=2)=[O:5])C.[Mg]>CO.ClCCl>[CH3:1][O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][CH3:16])[CH:12]=2)[NH:7]1)=[O:5]

Participants

5

Reactant 2

HCID 20926Ethyl 5-methoxyindole-2-carboxylateHCID 5462224Magnesium

Product 1

HCID 54121458(RS)-5-methoxy-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
7.5 °C

Procedure

5-Methoxyindole-2-carboxylic acid ethyl ester (2 g, 9.13 mmol) and magnesium turnings (0.432 g, 18 mmol) were suspended in dried methanol (30 ml). This mixture was stirred at 5 to 10° C. under nitrogen for 3 hours, then poured into dichloromethane (200 ml), and washed with saturated ammonium chloride solution. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (3×100 ml). The combined organic layers were dried over sodium sulphate and evaporated. A brown solid was obtained. After column chromatography on silica gel using dichloromethane as eluent, a brown solid was obtained.

Workup

  1. washwashed with saturated ammonium chloride solution
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (3×100 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. customevaporated
  6. customA brown solid was obtained
  7. customa brown solid was obtained

Sources & evidence

ORD record
ord-0722b996b23a4ef6b513e95a8bd31185
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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