(1S)-(+)-Camphor-10-sulphonic acid → (1R,2R,4S)-(+)-Bicyclo[2.2.1]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine

HRID 1066727Notes

Reaction equation

HRID 1066727 reaction equation
[CH3:1][CH:2]([NH:8][C:9]1[CH:18]=[N:17][C:16]2[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[CH:15]=2)[N:10]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CCCCCCC>[C@H:3]12[CH2:7][C@H:6]([CH2:5][CH2:4]1)[CH2:1][C@H:2]2[NH:8][C:9]1[CH:18]=[N:17][C:16]2[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[CH:15]=2)[N:10]=1

Participants

4

Reactant 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 54383944HCID 54383944, compound

Product 1

HCID 57045267(1R,2R,4S)-(+)-Bicyclo[2.2.1]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

The (±)-bicyclo[2.2.]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine of Example 14 is resolved on a chiral HPLC column (Chiralpac AD, 25×2 cm, 60% heptane/40% ethanol with 10 mM (1S)-(+)-camphorsulfonic acid, 12 mL/minute) and the above titled product is obtained as the first eluent. The fractions collected are combined and washed with 50 mL of 1 N NaOH before drying (MgSO4). The solution after filtration is concentrated on a rotovap and then dried under a high vacuum. A yellow solid is obtained. [α]d2+19.5° (c=0.20, CH2Cl2) m.p. 184-186° C. Anal. calcd for C17H21N3O2×0.3H2O: C, 66.90; H, 7.15; N, 13.77. Found: C, 66.86; H, 7.01; N, 13.86.

Sources & evidence

ORD record
ord-14e874def7784b8da4978fdc60f8dc99
Source dataset
uspto-grants-2001_06
Patent number
US06245760B1

Reaction notes

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