Ammonium formate → HCID 58928359, compound

HRID 851952Notes

Reaction equation

HRID 851952 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]2[C@@H:14]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH3:26])[C:19]=3[CH3:27])[CH2:15][CH2:16][CH2:17][C@H:10]2[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[OH-].[OH-].[Pd+2]>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([C@@H:14]2[N:11]3[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]3[CH2:17][CH2:16][CH2:15]2)=[C:19]([CH3:27])[C:20]=1[CH3:26]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 58928364HCID 58928364, compound

Product 1

HCID 58928359HCID 58928359, compound

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

A solution containing the compound obtained in step 3 (2.66 g, 7.30 mmol) and ammonium formate (6.90 g, 109.50 mmol, 15 eq) is treated with 665 mg of 20% palladium hydroxide on carbon, and heated at reflux under a nitrogen balloon for 2 h. The mixture is filtered through a CELITE pad. The pad is washed with 200 mL of chloroform and the solution is concentrated in vacuo. The residue is taken up in 200 mL dichloromethane and washed with 1N NaOH, water and brine (75 mL each) to remove any residual ammonium formate. The organic solution is concentrated in vacuo to afford (6R,9aS)-6-(4-methoxy-2,3-dimethylphenyl)-octahydro-pyrido[1,2-a]pyrazine as an amber colored oil which is used in the next step with no further purification. LC/MS: 275 (M+1). 1H NMR (400 MHz, CDCl3): 7.36 (1H, dd), 6.74 (1H, dd), 4.50 (1H, dd), 3.80 (3H, s), 3.28 (1H, d), 2.86 (1H, dd), 2.78 (2H, m), 2.67-2.55 (3H, m), 2.22 (3H, s), 2.17 (3H, s), 1.78-1.67 (4H, bm), 1.56-1.31 (4H, bm).

Workup

  1. temperatureheated
  2. temperatureat reflux under a nitrogen balloon for 2 h
  3. filtrationThe mixture is filtered through a CELITE pad
  4. washThe pad is washed with 200 mL of chloroform
  5. concentrationthe solution is concentrated in vacuo
  6. washwashed with 1N NaOH, water and brine (75 mL each)
  7. customto remove any residual ammonium formate
  8. concentrationThe organic solution is concentrated in vacuo

Sources & evidence

ORD record
ord-1ee14403e61d475cbc4d94c14e407a5e
Source dataset
uspto-grants-2007_08
Patent number
US07253168B2

Reaction notes

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