Water → HCID 19036482, compound

HRID 264428Notes

Reaction equation

HRID 264428 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[N:8]([CH:11]([CH3:26])[CH2:12][N:13]1[CH:17]=[CH:16][C:15]2[CH2:18][C:19]3[C:24]([C:14]1=2)=CC(O)=[CH:21][CH:20]=3)=[N+:9]=[N-:10].N1C=CC=CC=1.O>ClCCl>[N:8]([CH:11]([CH3:26])[CH2:12][N:13]1[CH:17]=[CH:16][C:15]2[CH2:18][C:19]3[C:24]([C:14]1=2)=[CH:6][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:21][CH:20]=3)=[N+:9]=[N-:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 19036449HCID 19036449, compound

Product 1

HCID 19036482HCID 19036482, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.7 ml of acetic anhydride was added while stirring to a solution of 1.05 g of (RS)-1-(2-azido-propyl)-7-hydroxy-1,4-dihydro-indeno[1,2-b]pyrrol and 0.6 ml of pyridine in 30 ml of dichloromethane and the mixture was stirred for an additional 16 hours. Subsequently, the reaction mixture was treated with 50 ml of dichloromethane and 40 ml of water. The organic phase was separated and this was washed once with 50 ml of saturated sodium chloride solution. After drying over magnesium sulfate, the solution was concentrated in a vacuum and the crude product was purified by column chromatography on silica gel (ethyl acetate/hexane 1:2). 0.9 g (85%) of (RS)-1-(2-azido-propyl)-7-acetoxy-1,4-dihydro-indeno[1,2-b]pyrrole was obtained as a light orange oil.

Workup

  1. customThe organic phase was separated
  2. washthis was washed once with 50 ml of saturated sodium chloride solution
  3. dry with materialAfter drying over magnesium sulfate
  4. concentrationthe solution was concentrated in a vacuum
  5. customthe crude product was purified by column chromatography on silica gel (ethyl acetate/hexane 1:2)

Sources & evidence

ORD record
ord-1c3eb78cb58c4a6fb0143999091bb53d
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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