N-bromobutanimide → HCID 131727478, compound

HRID 1985709Notes

Reaction equation

HRID 1985709 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH:22]([C:27]([CH3:32])([CH3:31])[CH:28]([CH3:30])[CH3:29])[O:23][SiH:24]([CH3:26])[CH3:25])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:33]N1C(=O)CCC1=O>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH:22]([C:27]([CH3:31])([CH3:32])[CH:28]([CH3:29])[CH3:30])[O:23][SiH:24]([CH3:26])[CH3:25])=[C:14]([Br:33])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 131727479HCID 131727479, compound

Product 1

HCID 131727478HCID 131727478, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 22.78 g (4R,9aR)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 200 ml tetrahydrofuran was added at 0° C. 8.78 g (0.049 mol) N-bromosuccinimide and the mixture was stirred at 0° C. for 30 minutes. The reaction mixture was diluted with 500 ml ethyl acetate and extracted sequentially with a 10% aqueous solution of sodium thiosulfate, a 10% aqueous solution of citric acid, water and brine dried over sodium sulfate, evaporated under aspirator vacuum and dried to constant weight under high vacuum to yield 26.5 g of the title compound as colorless oil. (MS: 541 (M+H+)).

Workup

  1. extractionextracted sequentially with a 10% aqueous solution of sodium thiosulfate
  2. dry with materiala 10% aqueous solution of citric acid, water and brine dried over sodium sulfate
  3. customevaporated under aspirator vacuum
  4. customdried to constant weight under high vacuum

Sources & evidence

ORD record
ord-dc67aa3bdc53455c98b849f4ad2e742a
Source dataset
uspto-grants-2009_06
Patent number
US07547699B2

Reaction notes

Loading…