tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate → (3S)-tert-Butyl 4-(6-Aminopyridin-3-yl)-3-methylpiperazine-1-carboxylate

HRID 1021869Notes

Reaction equation

HRID 1021869 reaction equation
NC1N=CC(N2CCN(C(OC(C)(C)C)=O)CC2)=CC=1.[CH3:21][C@@H:22]1[N:27]([C:28]2[CH:29]=[N:30][C:31]([N+:34]([O-])=O)=[CH:32][CH:33]=2)[CH2:26][CH2:25][N:24]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:23]1>>[NH2:34][C:31]1[N:30]=[CH:29][C:28]([N:27]2[CH2:26][CH2:25][N:24]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:23][C@@H:22]2[CH3:21])=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 11737525tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylateHCID 86683728tert-butyl (3S)-3-methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylate

Product 1

HCID 86683730(3S)-tert-Butyl 4-(6-Aminopyridin-3-yl)-3-methylpiperazine-1-carboxylateYield 93.1%

Procedure

Following the procedure described for compound 101h and starting with (3S)-tert-butyl 3-methyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylate 191e (5.8 g, 18 mmol) afforded 191f as a brown solid (4.9 g, 93%). MS-ESI: [M+H]+ 293

Sources & evidence

ORD record
ord-71f2a394d1ab4d25acc1cef045888518
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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