5-Methoxy-2-methylindole → (S)-[2-(5-Methoxy-2-methyl-indol-1-yl)-1-methyl-ethyl]-carbamic Acid Tert-Butyl Ester

HRID 2249584Notes

Reaction equation

HRID 2249584 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[CH:6]2.CC([O-])(C)C.[K+].[C:19]([O:23][C:24]([N:26]1[C@@H:30]([CH3:31])[CH2:29]OS1(=O)=O)=[O:25])([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C>[C:19]([O:23][C:24](=[O:25])[NH:26][C@@H:30]([CH3:29])[CH2:31][N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH:6]=[C:7]1[CH3:12])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 706425-Methoxy-2-methylindoleHCID 109882941,2,3-Oxathiazolidine-3-carboxylic acid, 4-methyl-, 1,1-dimethylethyl ester, 2,2-dioxide, (4S)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 67031612(S)-[2-(5-Methoxy-2-methyl-indol-1-yl)-1-methyl-ethyl]-carbamic Acid Tert-Butyl EsterYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5-Methoxy-2 methylindole (806 mg) was dissolved in DMF (25 mL) and cooled to 0° C. with an ice bath. Potassium tert-butylate (1M in THF, 6 mL) was added over 15 minutes and the resulting mixture was allowed to stir for further 30 minutes. (S)-4-Methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester IV (1.42 g) was added in one portion and stirring was continued at RT until TLC analysis showed complete consumption of the starting material. The reaction mixture was partitioned between ether and saturated NH4Cl solution and the organic layer was separated, washed with sat. NH4Cl and brine, dried over Na2SO4, filtered and evaporated in vacuo. The residue was purified by flash chromatography (CH2Cl2). The appropriate fractions were combined and evaporated to give the product as an off-white solid (1.42 g).

Workup

  1. stirringstirring
  2. customwas continued at RT until TLC analysis
  3. customconsumption of the starting material
  4. customThe reaction mixture was partitioned between ether and saturated NH4Cl solution
  5. customthe organic layer was separated
  6. washwashed with sat. NH4Cl and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified by flash chromatography (CH2Cl2)
  11. customevaporated

Sources & evidence

ORD record
ord-41f6265c38f04188b0633e7c12ea02e6
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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