tert-Butyl (2S)-2-(aminomethyl)piperidine-1-carboxylate → (S)-2-[(6,7-Difluoroquinoxalin-2-ylamino)methyl]-piperidine-1-carboxylic acid tert buty ester

HRID 2113519Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[CH:26]=[N:25][C:24]2[C:19](=[CH:20][C:21]([F:28])=[C:22]([F:27])[CH:23]=2)[N:18]=1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH:15][C:26]1[CH:17]=[N:18][C:19]2[C:24](=[CH:23][C:22]([F:27])=[C:21]([F:28])[CH:20]=2)[N:25]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

(S)-2-Aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (0.607 g), and 2-chloro-6,7-difluoroquinoxaline McQuaid et al. J. Med Chem. (1992), 35(18), 3319-24 (0.569 g) were dissolved in dimethylformamide (1 ml) and heated to 90 ° C. for 5 days under an atmosphere of argon. After cooling, the reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with water, saturated brine, dried and evaporated. The residue was chromatographed over silica gel, eluting with a gradient of 10 to 50% ethyl acetate in hexane. The title compound was obtained as a pale yellow solid (0.460 g), MH+ 379.

Workup

temperatureAfter cooling
customthe reaction solution was partitioned between ethyl acetate and water
washThe organic layer was washed with water, saturated brine
customdried
customevaporated
customThe residue was chromatographed over silica gel
washeluting with a gradient of 10 to 50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-2c867b79880d48b5b1ca1d607b2f55d0
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432270B2

Reaction notes

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