Indole → ethyl trans-2-((1H-indol-1-yl)methyl)cyclopropanecarboxylate

HRID 511849Notes

Reaction equation

HRID 511849 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.CS(O[CH2:17][CH:18]1[CH2:20][CH:19]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])(=O)=O.O>CN(C=O)C>[N:3]1([CH2:17][C@@H:18]2[CH2:20][C@H:19]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 24758Sodium hydrideHCID 57184993Ethyl 2-(((methylsulfonyl)oxy)methyl)cyclopropanecarboxylate

Product 1

HCID 67290699ethyl trans-2-((1H-indol-1-yl)methyl)cyclopropanecarboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 55 mg, 1.4 mmol) in DMF (5 mL) was added indole (135 mg, 1.2 mmol). After stirring at room temperature for 10 min, ethyl 2-(((methylsulfonyl)oxy)methyl)cyclopropanecarboxylate (307 mg, 1.4 mmol) was added. After stirring at room temperature for 6 h, the mixture was poured into water, and the aqueous layer was extracted with EtOAc twice. The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (10:1-5:1) to give 153 mg (54%) of the title compound as a pale brown oil;

Workup

  1. stirringAfter stirring at room temperature for 6 h
  2. extractionthe aqueous layer was extracted with EtOAc twice
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (10:1-5:1)

Sources & evidence

ORD record
ord-0f75e6b3148947f98c16685a91637156
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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