Diisopropylethylamine → trans(+/-)-N,N-di-BOC-4-methoxy-1-(3-nitropyridin-4-yl)-piperidin-3-amine

HRID 73523Notes

Reaction equation

HRID 73523 reaction equation
[C:1]([O:5][C:6]([N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:9]1[C@H:14]([O:15][CH3:16])[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:25]1[CH:30]=[CH:29][N:28]=[CH:27][C:26]=1[N+:31]([O-:33])=[O:32].CCN(C(C)C)C(C)C>CCOC(C)=O>[C:6]([N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:9]1[C@H:14]([O:15][CH3:16])[CH2:13][CH2:12][N:11]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])[CH2:10]1)([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27357814-Chloro-3-nitropyridineHCID 86644734trans(+/-)-3-(Bis(tert-butoxycarbonyl)amino)-4-methoxypiperidine

Product 1

HCID 86644733trans(+/-)-N,N-di-BOC-4-methoxy-1-(3-nitropyridin-4-yl)-piperidin-3-amineYield 59%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Method 1 was followed using trans (+/−)-3-(bis(tert-butoxycarbonyl)amino)-4-methoxypiperidine (1.0 equiv.), 4-chloro-3-nitropyridine (1.2 equiv.), and DIEA (4.0 equiv.) to give trans (+/−)-N,N-di-BOC-4-methoxy-1-(3-nitropyridin-4-yl)-piperidin-3-amine after column chromatography (EtOAc and hexanes, 50%) in 59% yield for two steps. LCMS (m/z): 453.2 (MH+), LC Rt=3.24 min.

Sources & evidence

ORD record
ord-83c220e4f2da420a967603f4be933acd
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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