Conessine → HCID 67424844, compound

HRID 1393021Notes

Reaction equation

HRID 1393021 reaction equation
[CH3:1][C@@H:2]1[N:25]([CH3:26])[CH2:24][C@:7]23[CH2:8][CH2:9][C@@H:10]4[C@@:15]5([CH3:23])[CH2:16][CH2:17][C@H:18]([N:20]([CH3:22])[CH3:21])[CH2:19][C:14]5=[CH:13][CH2:12][C@H:11]4[C@@H:6]2[CH2:5][CH2:4][C@H:3]13>C(OCC)(=O)C.[Pd]>[CH3:21][N:20]([CH3:22])[CH:18]1[CH2:19][CH:14]2[C:15]([CH3:23])([CH:10]3[CH:11]([CH2:12][CH2:13]2)[CH:6]2[CH2:5][CH2:4][CH:3]4[CH:2]([CH3:1])[N:25]([CH3:26])[CH2:24][C:7]24[CH2:8][CH2:9]3)[CH2:16][CH2:17]1

Participants

4

Reactant 1

HCID 441082Conessine

Product 1

HCID 67424844HCID 67424844, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Conessine (50 mg, 0.14 mmol) was dissolved in 3 mL ethyl acetate and 10% Pd/C (20 mg) was added under inert atmosphere. The reaction mixture was hydrogenated under a hydrogen balloon for 24 hours. Reaction was not complete by TLC. The reaction mixture was filtered through diatomaceous earth, washed with ethyl acetate, and the filtrate was concentrated to give the crude product which was purified by silica gel column eluted with 0.3% ammonium hydroxide and 3% methanol in dichloromethane to give the desired product (15 mg, 30% yield).

Workup

  1. customfor 24 hours
  2. customReaction
  3. filtrationThe reaction mixture was filtered through diatomaceous earth
  4. washwashed with ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. customto give the crude product which
  7. customwas purified by silica gel column
  8. washeluted with 0.3% ammonium hydroxide and 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-7d80e4dff4eb410385c6a5258e7d98c8
Source dataset
uspto-grants-2008_03
Patent number
US07345034B2

Reaction notes

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