m-Chloroperbenzoic acid → HCID 54588460, compound

HRID 447272Notes

Reaction equation

HRID 447272 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[N:14]=[CH:15][C:16]([NH:19][C:20]2[O:21][C@:22]3([CH2:30][N:31]=2)[CH:27]2[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]2)[CH2:23]3)=[N:17][CH:18]=1>C1COCC1>[Cl:12][C:13]1[N:14]=[CH:15][C:16]([NH:19][C:20]2[O:21][C@:22]3([CH2:30][N:31]=2)[CH:27]2[CH2:28][CH2:29][N+:24]([O-:6])([CH2:25][CH2:26]2)[CH2:23]3)=[N:17][CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 52920234HCID 52920234, compound

Product 1

HCID 54588460HCID 54588460, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Chlorobenzoperoxoic acid (104 mg, 0.466 mmol) was added to a solution of (R)—N-(5-chloropyrazin-2-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (114 mg, 0.388 mmol) in THF (3 mL) at room temperature and stirred for 2 h. The mixture was concentrated and the crude product was purified by flash chromatography on a 40 g silica gel cartridge with 10 to 30% [9:1 MeOH/NH4OH] in EtOAc, 30 min. Pure fractions were pooled, concentrated and dried. The residue was dissolved in EtOAC/MeOH 95:5, passed thru a 0.22 micron filter, concentrated and dried under high vacuum to yield (S)-2-(5-chloropyrazin-2-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (113 mg, 94% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe crude product was purified by flash chromatography on a 40 g silica gel cartridge with 10 to 30% [9:1 MeOH/NH4OH] in EtOAc, 30 min
  3. concentrationconcentrated
  4. customdried
  5. dissolutionThe residue was dissolved in EtOAC/MeOH 95:5
  6. filtrationfilter
  7. concentrationconcentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-6b312e20c3c24b62a1afda923986ffe8
Source dataset
uspto-grants-2013_07
Patent number
US08481555B2

Reaction notes

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