N-bromobutanimide → HCID 67238425, compound

HRID 1985719Notes

Reaction equation

HRID 1985719 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]([CH2:22][OH:23])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:24]N1C(=O)CCC1=O>O1CCCC1>[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]([CH2:22][OH:23])=[C:14]([Br:24])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67238448(4R,9aR)-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

HCID 67238425HCID 67238425, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.00 g (4R,9aR)-6-Hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 50 ml tetrahydrofuran was added at 0°° C. 2.75 g N-bromosuccinimide at once and the mixture was stirred at 0° C. for 1 h. The reaction mixture was partitioned between 10% sodium thiosulfate and ethyl acetate. The phases were separated and the organic phase was washed with 10% sodium bicarbonate and brine dried over magnesium sulfate and evaporated. The residue was triturated in ca 20 ml heptane:ethyl acetate 1:3 to yield 5.75 g of the title compound as white crystals melting at 110-112° C.

Workup

  1. customThe reaction mixture was partitioned between 10% sodium thiosulfate and ethyl acetate
  2. customThe phases were separated
  3. washthe organic phase was washed with 10% sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was triturated in ca 20 ml heptane:ethyl acetate 1:3

Sources & evidence

ORD record
ord-2871d9aea0444c658eb78d0fe49aa69f
Source dataset
uspto-grants-2009_06
Patent number
US07547699B2

Reaction notes

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