HCID 86625191, compound → HCID 86625192, compound

HRID 419381Notes

Reaction equation

HRID 419381 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH2:9][C@@H:8]2[CH2:10][C@H:5]1[CH2:6][N:7]2[CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]([O:26][CH3:27])[CH:18]=2)[CH2:13][CH2:12]1>CCOC(C)=O.[Pd]>[F:1][CH2:2][CH2:3][N:4]1[CH2:9][C@@H:8]2[CH2:10][C@H:5]1[CH2:6][N:7]2[CH:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([O:26][CH3:27])[CH:18]=2)[CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 86625191HCID 86625191, compound

Product 1

HCID 86625192HCID 86625192, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To (1S,4S)-2-(2-fluoroethyl)-5-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-2,5-diazabicyclo[2.2.1]heptane (0.22 g, 0.58 mmol) in EtOAc (10 mL) was added Pd (10%) on carbon (50 mg). The reaction was evacuated then refilled with H2 gas from a balloon. The reaction was stirred under a balloon atmosphere of H2 for 4 days. The reaction was evacuated and the atmosphere replaced with N2. The solution was filtered to remove Pd/C and rotovaped down to give the title compound of step D as a purple oil (200 mg, 0.57 mmol, 98% yield). 1H NMR (400 MHz, CDCl3) δ 6.62 (d, J=8.4 Hz, 1H), 6.51 (d, J=2.6 Hz, 1H), 6.41 (dd, J=8.4, 2.6 Hz, 1H), 4.62-4.39 (m, 2H), 3.82 (s, 3H), 3.57 (br s, 1H), 3.47-3.38 (m, 2H), 3.35 (br s, 1H), 2.98-2.56 (m, 8H), 2.46-2.39 (m, 1H), 1.97-1.53 (m, 6H).

Workup

  1. customThe reaction was evacuated
  2. additionthen refilled with H2 gas from a balloon
  3. customThe reaction was evacuated
  4. filtrationThe solution was filtered
  5. customto remove Pd/C

Sources & evidence

ORD record
ord-960509d1362a4cb48c411c793bb12396
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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