m-Chloroperbenzoic acid → HCID 54588455, compound

HRID 447269Notes

Reaction equation

HRID 447269 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH:12]1([O:17][C:18]2[N:23]=[CH:22][N:21]=[C:20]([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)[CH:19]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1>C1COCC1>[CH:12]1([O:17][C:18]2[N:23]=[CH:22][N:21]=[C:20]([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)[CH:19]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58088174HCID 58088174, compound

Product 1

HCID 54588455HCID 54588455, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

mCPBA (0.114 g, 0.510 mmol) was added to a solution of (R)—N-(6-(cyclopentyloxy)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.175 g, 0.510 mmol) in THF (15 ml). The mixture was stirred at room temperature for 18 h and concentrated. The residue was purified by silica gel chromatography (5-25% 9:1 methanol:ammonium hydroxide-ethyl acetate) to afford (S)-2-(6-(cyclopentyloxy)pyrimidin-4-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide an off-white solid (0.076 g, 0.207 mmol, 41%). 1H NMR (400 MHz, MeOD) δ ppm 8.38 (1H, s), 6.34 (1H, br. s.), 5.18-5.37 (1H, m), 4.01 (1H, d, J=11.08 Hz), 3.85 (1H, d, J=10.83 Hz), 3.58-3.75 (2H, m), 3.34-3.53 (3H, m), 3.20-3.27 (1H, m), 2.32-2.46 (1H, m), 2.23-2.31 (1H, m), 1.98-2.19 (3H, m), 1.93-1.99 (2H, m), 1.68-1.84 (4H, m), 1.55-1.70 (2H, m).

Workup

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

Sources & evidence

ORD record
ord-f819978f7cb84a56b1fe841afa7a1312
Source dataset
uspto-grants-2013_07
Patent number
US08481555B2

Reaction notes

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