m-Chloroperbenzoic acid → HCID 86664590, compound

HRID 447267Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12]2[O:13][C@@:14]3([CH2:22][N:23]=2)[CH:19]2[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]2)[CH2:15]3)[N:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:29]>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12]2[O:13][C@@:14]3([CH2:22][N:23]=2)[CH:19]2[CH2:18][CH2:17][N+:16]([O-:29])([CH2:21][CH2:20]2)[CH2:15]3)[N:2]=1

Participants

Reactant 2

HCID 70297m-Chloroperbenzoic acid

HCID 44479558HCID 44479558, compound

Product 1

HCID 86664590HCID 86664590, compoundYield 83.7%

Procedure

By a method similar to that used in Example 1, (S)—N-(isoquinolin-3-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (108 mg, 0.350 mmol) and 3-chlorobenzoperoxoic acid (72.5 mg, 0.420 mmol) gave (R)-2-(isoquinolin-3-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (95 mg, 83% yield). 1H NMR (500 MHz, MeOD) δ ppm 9.04 (1H, s), 7.97 (1H, d, J=8.24 Hz), 7.76 (1H, d, J=8.24 Hz), 7.61-7.67 (1H, m), 7.44-7.49 (2H, m), 4.03 (1H, d, J=10.99 Hz), 3.87 (1H, d, J=10.99 Hz), 3.65-3.77 (2H, m), 3.44-3.53 (3H, m), 3.27-3.31 (1H, m), 2.43-2.55 (1H, m), 2.32 (1H, br. s.), 2.04-2.22 (3H, m). LCMS: RT=0.54 min, MH+=325.2 [ Waters Acquity SDS: 2 to 98% B, 1 min gradient; hold 98% B, 0.5 min; flow rate 0.8 mL/min; Solvent A: 100% H2O/0.05% TFA; Solvent B: 100% ACN/0.05% TFA].

Sources & evidence

ORD record: ord-362e1e23323d43649d0f0e498768b0d8
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481555B2

Reaction notes

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