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

HRID 69901Notes

Reaction equation

HRID 69901 reaction equation
[F:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH2:4][CH:3]1[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21]>C(O)C.C(OCC)(=O)C>[NH2:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[N:5]1[CH2:6][CH2:7][CH:2]([F:1])[CH:3]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:4]1

Participants

4

Reactant 1

HCID 76773285(+/-)-Tert-butyl 4-fluoro-1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate

Product 1

HCID 76773287(+/-)-Tert-butyl 1-(3-aminopyridin-4-yl)-4-fluoropiperidin-3-ylcarbamateYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following Method 2 of Example 49, (+/−)-tert-butyl 4-fluoro-1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate in ethanol and ethyl acetate (1:1, 0.1 M solution) was reduced yielding (+/−)-tert-butyl 1-(3-aminopyridin-4-yl)-4-fluoropiperidin-3-ylcarbamate, (>99%). LCMS (m/z): 311.2 (MH+); LC Rt=2.14 min.

Sources & evidence

ORD record
ord-4d25aa0af77c474488a5f504e29ac43f
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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