Water → [2-(phenylmethyl)hexahydropyrrolo[1,2-a]pyrazin-8a(6H)-yl]methanol

HRID 2074855Notes

Reaction equation

HRID 2074855 reaction equation
O=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][C:5](=O)[N:4]2[CH2:16][CH2:17][CH2:18][C:3]12[C:19](OCC)=[O:20].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[C:9]1([CH2:8][N:7]2[CH2:6][CH2:5][N:4]3[CH2:16][CH2:17][CH2:18][C:3]3([CH2:19][OH:20])[CH2:2]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59215759ethyl 1,4-dioxo-2-(phenylmethyl)hexahydropyrrolo[1,2-a]pyrazine-8a(6H)-carboxylate

Product 1

HCID 59215761[2-(phenylmethyl)hexahydropyrrolo[1,2-a]pyrazin-8a(6H)-yl]methanolYield 46.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 1,4-dioxo-2-(phenylmethyl)hexahydropyrrolo[1,2-a]pyrazine-8a(6H)-carboxylate (D65, 450 mg) in anhydrous THF (5 mL) under a Nitrogen atmosphere at 0° C., lithium aluminium hydride (1M in THF, 14 mL) was added dropwise. The resulting mixture was stirred at 0° C. for 10 minutes, then allowed to reach rt and stirred at this temperature for 45 minutes. It was then heated at reflux temperature for 3.5 hours and then allowed to cool to r.t. Water (540 microL), NaOH (1M solution, 540 microL) and water (1.6 mL) were then added to the solution and the formation of a white precipitate was observed. The suspension was stirred at rt for 30-40 minutes then filtered over a Gooch funnel. The organic filtrate was dried and concentrated in vacuo to a residue which was purified by flash chromatography (DCM/MeOH from 100/0 to 90:10) to give the desired compound (162 mg) as orange oil.

Workup

  1. customto reach rt
  2. stirringstirred at this temperature for 45 minutes
  3. temperatureIt was then heated
  4. temperatureat reflux temperature for 3.5 hours
  5. temperatureto cool to r.t
  6. stirringThe suspension was stirred at rt for 30-40 minutes
  7. filtrationthen filtered over a Gooch funnel
  8. customThe organic filtrate was dried
  9. concentrationconcentrated in vacuo to a residue which
  10. customwas purified by flash chromatography (DCM/MeOH from 100/0 to 90:10)

Sources & evidence

ORD record
ord-c3318ac7e2084262a0c8e47cb391866e
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

Loading…