N-bromobutanimide → HCID 68997171, compound

HRID 656403Notes

Reaction equation

HRID 656403 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@:6]1([C:14](=[O:15])[NH:13][C:12](=[O:16])[N:11]1[CH3:17])[CH2:5]2.[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:3]([Br:18])=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@:6]1([C:14](=[O:15])[NH:13][C:12](=[O:16])[N:11]1[CH3:17])[CH2:5]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57774196HCID 57774196, compound2×

Product 1

HCID 68997171HCID 68997171, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(R)-5′-Amino-3-methyl-spiro[imidazolidine-4,2′-indane]-2,5-dione (580 mg, 2.51 mmol, described in Intermediate 8) was suspended in CHCl3 (250 mL) and N-bromosuccinimide (335 mg, 1.88 mmol) was added in one portion. The resulting mixture was stirred at ambient temperature for 40 min, then washed with dilute aqueous NaHCO3 (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc—100:0 to 0:100, to give (R)-5′-amino-4′-bromo-3-methyl-spiro[imidazolidine-4,2′-indane]-2,5-dione, which eluted first, and the title compound, which eluted second. MS: m/z=353 (M+1+CH3CN).

Workup

  1. washwashed with dilute aqueous NaHCO3 (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-c1095d280f364b77986f4b29ed3c43a0
Source dataset
uspto-grants-2011_12
Patent number
US08071771B2

Reaction notes

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