m-Chloroperbenzoic acid → HCID 54588500, compound

HRID 447276Notes

Reaction equation

HRID 447276 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:12][C:13]2[O:14][C@:15]3([CH2:23][N:24]=2)[CH:20]2[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]2)[CH2:16]3)[N:3]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:12][C:13]2[O:14][C@:15]3([CH2:23][N:24]=2)[CH:20]2[CH2:19][CH2:18][N+:17]([O-:33])([CH2:22][CH2:21]2)[CH2:16]3)[N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67466948HCID 67466948, compound

Product 1

HCID 54588500HCID 54588500, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To (R)—N-(1-Fluoroisoquinolin-3-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.063 g, 0.193 mmol) in CHCl3 (15 mL) was added m-CPBA (0.034 g, 0.195 mmol) at room temperature. The reaction was stirred at room temperature for 3 hours. TLC showed lower spot and no starting material. The mixture was purified by chromatography (Biotage: 15-20% of 9:1 MeOH:NH4OH in CHCl3; ˜1.1 L) to yield the pure fractions. The fractions were combined and the solvent was removed to yield (S)-2-(1-fluoroisoquinolin-3-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (0.050 g, 0.146 mmol, 76% yield) as a white powder. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.12-8.42 (m, 1H), 8.01 (d, J=8.2 Hz, 1H), 7.86 (br. s., 1H), 7.73 (br. s., 1H), 7.43-7.60 (m, 1H), 6.93-7.35 (m, 1H), 3.69-4.05 (m, 1H), 3.58 (br. s., 1H), 3.00-3.33 (m, 6H), 2.19 (br. s., 2H), 1.94 (d, J=10.1 Hz, 3H). LC/MS: retention time 1.78 (M+1=343.1).

Workup

  1. customThe mixture was purified by chromatography (Biotage: 15-20% of 9:1 MeOH:NH4OH in CHCl3; ˜1.1 L)
  2. customto yield the pure fractions
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-e02abafdeffe472eb5535a8ccb7b227a
Source dataset
uspto-grants-2013_07
Patent number
US08481555B2

Reaction notes

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