Ammonium formate → (Octahydropyrrolo[1,2-a]pyrazin-8a-yl)methanol

HRID 421209Notes

Reaction equation

HRID 421209 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][N:11]3[CH2:14][CH2:15][CH2:16][C:10]3([CH2:17][OH:18])[CH2:9]2)C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH2:9]1[NH:8][CH2:13][CH2:12][N:11]2[CH2:14][CH2:15][CH2:16][C:10]12[CH2:17][OH:18]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59215761[2-(phenylmethyl)hexahydropyrrolo[1,2-a]pyrazin-8a(6H)-yl]methanol

Product 1

HCID 45122045(Octahydropyrrolo[1,2-a]pyrazin-8a-yl)methanolYield 105.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [2-(phenylmethyl)hexahydropyrrolo[1,2-a]pyrazin-8a(6H)-yl]methanol (D66, 180 mg) in anhydrous methanol (5 mL) under a Nitrogen atmosphere at rt, ammonium formate (475 mg) and palladium (10% on carbon, 13 mg) were added. The resulting suspension was heated at reflux temperature for 3.5 hours, then allowed to cool to r.t. and filtered over Celite. The organic extract was dried and concentrated in vacuo to give the desired compound (120 mg) as orange waxy solid.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux temperature for 3.5 hours
  3. filtrationfiltered over Celite
  4. extractionThe organic extract
  5. customwas dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e79ee58d489b4fad9709b3b7fcd306ce
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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