m-Chloroperbenzoic acid → HCID 54588457, compound

HRID 447268Notes

Reaction equation

HRID 447268 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[C:12]1([CH3:37])[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:19]=[N:20][C:21]([NH:24][C:25]3[O:26][C@:27]4([CH2:35][N:36]=3)[CH:32]3[CH2:33][CH2:34][N:29]([CH2:30][CH2:31]3)[CH2:28]4)=[N:22][CH:23]=2)[CH:13]=1>C1COCC1>[C:12]1([CH3:37])[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:19]=[N:20][C:21]([NH:24][C:25]3[O:26][C@:27]4([CH2:35][N:36]=3)[CH:32]3[CH2:31][CH2:30][N+:29]([O-:9])([CH2:34][CH2:33]3)[CH2:28]4)=[N:22][CH:23]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58081870HCID 58081870, compound

Product 1

HCID 54588457HCID 54588457, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

mCPBA (0.074 g, 0.332 mmol) was added to a suspension of (R)—N-(5-m-tolylpyrimidin-2-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.116 g, 0.332 mmol) in THF (10 ml). The mixture was stirred at room temperature for 18 h, concentrated and purified by silica gel chromatography (5-25% 9:1 methanol:ammonium hydroxide-ethyl acetate) to afford (S)-2-(5-m-tolylpyrimidin-2-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide as an off-white solid (0.067 g, 0.176 mmol, 53%). 1H NMR (400 MHz, MeOD) δ ppm 8.79 (2H, s), 7.27-7.49 (3H, m), 7.20 (1H, d, J=7.55 Hz), 4.03 (1H, d, J=10.32 Hz), 3.88 (1H, d, J=10.58 Hz), 3.59-3.77 (2H, m), 3.38-3.52 (3H, m), 3.21-3.28 (1H, m), 2.40-2.52 (1H, m), 2.28-2.35 (1H, m), 1.96-2.21 (3H, m). LC/MS RT=1.71; [M+H]+=366.34.

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography (5-25% 9:1 methanol:ammonium hydroxide-ethyl acetate)

Sources & evidence

ORD record
ord-74315b12fe604ecdb5b86bd62cc5698b
Source dataset
uspto-grants-2013_07
Patent number
US08481555B2

Reaction notes

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