(+/-)-Tert-butyl 3-(tert-butyldimethylsilyloxy)-1-(3-nitropyridin-4-yl)piperidin-4-ylcarbamate → (+/-)-Tert-butyl 1-(3-aminopyridin-4-yl)-3-(tert-butyldimethylsilyloxy)piperidin-4-ylcarbamate

HRID 69900Notes

Reaction equation

HRID 69900 reaction equation
[Si:1]([O:8][CH:9]1[CH:14]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:13][CH2:12][N:11]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[N+:29]([O-])=O)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)C.C(OCC)(=O)C>[NH2:29][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][C:23]=1[N:11]1[CH2:12][CH2:13][CH:14]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])[CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10]1

Participants

4

Reactant 1

HCID 77419822(+/-)-Tert-butyl 3-(tert-butyldimethylsilyloxy)-1-(3-nitropyridin-4-yl)piperidin-4-ylcarbamate

Product 1

HCID 77419825(+/-)-Tert-butyl 1-(3-aminopyridin-4-yl)-3-(tert-butyldimethylsilyloxy)piperidin-4-ylcarbamateYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following Method 2 of Example 49, (+/−)-tert-butyl 3-(tert-butyldimethylsilyloxy)-1-(3-nitropyridin-4-yl)piperidin-4-ylcarbamate in ethanol and ethyl acetate (1:1, 0.1 M solution) was reduced yielding (+/−)-tert-butyl 1-(3-aminopyridin-4-yl)-3-(tert-butyldimethylsilyloxy)piperidin-4-ylcarbamate, (>99%). LCMS (m/z): 423.3 (MH+); LC Rt=3.62 min.

Sources & evidence

ORD record
ord-02a8820afc2e4e17a313c9e96e3679f2
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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