Methyl (3S,4R)-4-amino-1-[2-(5,7-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidine-3-carboxylate → Cis(+/-)1-{2-[4-amino-3-hydroxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one

HRID 255199Notes

Reaction equation

HRID 255199 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2[C:21]3[C:16](=[C:17]([F:23])[CH:18]=[C:19]([F:22])[CH:20]=3)[CH:15]=[CH:14][C:13]2=[O:24])[CH2:6][C@H:5]1[OH:25])=[N+]=[N-].N[C@@H]1CCN(CCN2C3C(=C(F)C=C(F)C=3)C=CC2=O)C[C@@H]1C(OC)=O>>[NH2:1][C@H:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2[C:21]3[C:16](=[C:17]([F:23])[CH:18]=[C:19]([F:22])[CH:20]=3)[CH:15]=[CH:14][C:13]2=[O:24])[CH2:6][C@H:5]1[OH:25]

Participants

3

Reactant 2

HCID 66775175Methyl (3S,4R)-4-amino-1-[2-(5,7-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]piperidine-3-carboxylateHCID 86642608Cis(+/-)1-{2-[4-azido-3-hydroxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one2×

Product 1

HCID 86642607Cis(+/-)1-{2-[4-amino-3-hydroxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one

Procedure

Cis(±)1-{2-[4-azido-3-hydroxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one (Intermediate 43) (190 mg, 0.54 mmol) was hydrogenated as described for Intermediate 34, for 3 hours, to give the product as a colorless oil, 175 mg (quantitative).

Sources & evidence

ORD record
ord-cc8c877e3fe14dc58eafa12656334e73
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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