m-Chloroperbenzoic acid → HCID 54588499, compound

HRID 447275Notes

Reaction equation

HRID 447275 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[O:16][C@:17]4([CH2:25][N:26]=3)[CH:22]3[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]3)[CH2:18]4)[CH:9]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:35])C=1>C1COCC1>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[O:16][C@:17]4([CH2:25][N:26]=3)[CH:22]3[CH2:23][CH2:24][N+:19]([O-:35])([CH2:20][CH2:21]3)[CH2:18]4)[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59286601HCID 59286601, compound

Product 1

HCID 54588499HCID 54588499, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)—N-(6-Fluoro-3,4′-bipyridin-2′-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.11 g, 0.311 mmol) in THF (10 mL) was treated with m-CPBA (0.059 g, 0.342 mmol) and stirred at room temperature for 2 hours. Reaction was complete by TLC and the product was purified by chromatography (Biotage: 5-20% of 8:2 MeOH:NH4OH in CHCl3) and the pure fractions were combined to yield (S)-2-(6-fluoro-3,4′-bipyridin-2′-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (0.05 g, 0.134 mmol, 43.1% yield) as a yellow powder. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.11 (br. s., 1H), 8.64 (br. s., 1H), 8.21-8.43 (m, 2H), 7.04-7.44 (m, 3H), 3.77 (d, J=10.1 Hz, 2H), 2.98-3.65 (m, 6H), 2.18 (br. s., 2H), 1.74-2.01 (m, 3H). LC/MS: retention time 0.78 (M+1=370.2).

Workup

  1. customReaction
  2. customthe product was purified by chromatography (Biotage: 5-20% of 8:2 MeOH:NH4OH in CHCl3)

Sources & evidence

ORD record
ord-72e179aff4a9404eb0eecd9e9323c0cd
Source dataset
uspto-grants-2013_07
Patent number
US08481555B2

Reaction notes

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