(6R,9R)-6-(2,3-difluorophenyl)-3-nitro-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol → (6R,9R)-3-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol

HRID 1099179Notes

Reaction equation

HRID 1099179 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:22][CH2:21][C@@H:20]([OH:23])[C:12]2=[N:13][CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=[C:11]2[CH2:10]1>CO.[Pd]>[NH2:17][C:15]1[CH:16]=[C:11]2[CH2:10][C@H:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])[CH2:22][CH2:21][C@@H:20]([OH:23])[C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 1

HCID 57911471(6R,9R)-6-(2,3-difluorophenyl)-3-nitro-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol

Product 1

HCID 57911417(6R,9R)-3-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of Pd/C (37 mg, 0.035 mmol) and (6R,9R)-6-(2,3-difluorophenyl)-3-nitro-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol (300 mg, 0.937 mmol) in methanol (10 mL) was hydrogenated under H2 (balloon) for 4 h. LCMS showed the reaction was over. The reaction was filtered through a celite plug. The filtrate was concentrated to give the crude product. MS (ESI)[M+H+]=291.29; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.84 (br. s., 1H) 7.02 (br. s., 3H) 6.79 (br. s., 1H) 5.90 (br. s., 1H) 4.74 (d, J=10.32 Hz, 1H) 3.87 (br. s., 2H) 3.06 (t, J=12.34 Hz, 1H) 2.86 (br. s., 1H) 2.62 (d, J=13.85 Hz, 1H) 2.26 (d, J=12.34 Hz, 1 H) 1.96-2.12 (m, 3H) 1.52 (br. s., 1H).

Workup

  1. filtrationThe reaction was filtered through a celite plug
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6bab5472af4b4456a1027b5a46a9b470
Source dataset
uspto-grants-2012_03
Patent number
US08143403B2

Reaction notes

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