(R)-4-(3-(tert-butyl dimethylsilyloxy)piperidin-1-yl)-3-nitropyridine → tert-butyl(S)-4-(3-(tert-butyldimethylsilyloxy)piperidin-1-yl)pyridin-3-amine

HRID 69918Notes

Reaction equation

HRID 69918 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[N+:21]([O-])=O)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)C>[C:4]([C:17]1[C:16]([NH2:21])=[C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10]2)[CH:20]=[CH:19][N:18]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

3

Reactant 1

HCID 68160972(R)-4-(3-(tert-butyl dimethylsilyloxy)piperidin-1-yl)-3-nitropyridine

Product 1

HCID 86669191tert-butyl(S)-4-(3-(tert-butyldimethylsilyloxy)piperidin-1-yl)pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following Method 2 of Example 49, (R)-4-(3-(tert-butyl dimethylsilyloxy)piperidin-1-yl)-3-nitropyridine in ethanol was reduced yielding tert-butyl (S)-4-(3-(tert-butyldimethylsilyloxy)piperidin-1-yl)pyridin-3-amine. LCMS (m/z): 308.2 (MH+); LC Rt=3.47 min.

Sources & evidence

ORD record
ord-11ab70d2f5ca4b6c9af1277e89f45388
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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