Dimethylformamide → HCID 20094833, compound

HRID 274093Notes

Reaction equation

HRID 274093 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:18])[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].CN(C)C=O>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:18][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetate2×HCID 11430Potassium Carbonate2×HCID 22719625HCID 22719625, compound

Product 1

HCID 20094833HCID 20094833, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-tert-butoxycarbonyl-5-hydroxyindan-2-amine (0.42 g), potassium carbonate (0.34 g), ethyl bromoacetate (0.24 ml), and N,N-dimethylformamide (4.2 ml) was stirred at ambient temperature for 20 hours. An additional portion of ethyl bromoacetate (0.12 ml) and potassium carbonate (0.17 g) was added to the mixture, and stirring was continued for an additional 12 hours. The mixture was diluted with ethyl acetate and the precipitates were filtered off. The filtrate was concentrated in vacuo, and the residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification of the residue by column chromatography on silica gel (eluent; 5:1 n-hexane-ethyl acetate) to give N-tert-butoxycarbonyl-5-ethoxycarbonylmethoxyindan-2-amine (0.44 g).

Workup

  1. stirringstirring
  2. waitwas continued for an additional 12 hours
  3. filtrationthe precipitates were filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by column chromatography on silica gel (eluent; 5:1 n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-34ec5b3c33bd47afa9bdbb28e6c24d8f
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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