Benzaldehyde → HCID 68442225, compound

HRID 2216588Notes

Reaction equation

HRID 2216588 reaction equation
CCN(CC)CC.[C:8]1([CH:14]=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH2:17]([O:19][C:20]([C:22]1[N:23]=[C:24]2[CH2:29][NH:28][CH2:27][CH2:26][N:25]2[CH:30]=1)=[O:21])[CH3:18].[BH3-]C#N.[Na+]>CCO>[CH2:17]([O:19][C:20]([C:22]1[N:23]=[C:24]2[CH2:29][N:28]([CH2:14][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:27][CH2:26][N:25]2[CH:30]=1)=[O:21])[CH3:18]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 11845779HCID 11845779, compound

Product 1

HCID 68442225HCID 68442225, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Et3N (6.27 mL), PhCHO (4.92 mL) were added successively to the EtOH (81 mL) solution of 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester, hydrochloride (9.47 g) at room temperature and stirred for 3 h under a nitrogen atmosphere. Then NaBH3CN (2.97 g) was added to the reaction mixture and stirred for 19 h. The mixture was filtered through a pad of Celite and diluted with CH2Cl2 and washed with 50% K2CO3 aq. The organic layer was dried (K2CO3) and filtered. The filtrate was concentrated under reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with CHCl3-acetone (1/0˜9/1) and CHCl3-MeOH (19/1˜9/1). The titled compound was obtained as pale yellow crystals (4.16 g, 36%).

Workup

  1. stirringstirred for 19 h
  2. filtrationThe mixture was filtered through a pad of Celite
  3. additiondiluted with CH2Cl2
  4. washwashed with 50% K2CO3 aq. The organic layer
  5. dry with materialwas dried (K2CO3)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. washthe column was eluted with CHCl3-acetone (1/0˜9/1) and CHCl3-MeOH (19/1˜9/1)

Sources & evidence

ORD record
ord-65ee872a51fe4f89bb9ab3eb7de1de7d
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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