Dichloromethane → HCID 21941423, compound

HRID 1158885Notes

Reaction equation

HRID 1158885 reaction equation
CC(C[AlH]CC(C)C)C.C(Cl)Cl.C([O:15][C:16]([C:18]1[N:19]=[C:20]2[CH2:25][N:24]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:23][CH2:22][N:21]2[CH:33]=1)=O)C>C1(C)C=CC=CC=1>[CH2:26]([N:24]1[CH2:23][CH2:22][N:21]2[CH:33]=[C:18]([CH:16]=[O:15])[N:19]=[C:20]2[CH2:25]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14487Diisobutylaluminum hydrideHCID 68442225HCID 68442225, compound

Product 1

HCID 21941423HCID 21941423, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.01 M solution of DIBAL in toluene (1 mL+0.2 mL+0.3 mL) was added to the dry CH2Cl2 (5 mL) solution of 7-benzyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester (283 mg) under a nitrogen atmosphere at −78° C. and stirred for 1.5 h. The mixture was quenched with 1 M HCl (5 mL). The reaction mixture was filtered through a pad of Celite. The filtrate was washed with 50% K2CO3 aq. and the aqueous layer was extracted with CH2Cl2. The combined 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 (9/1˜4/1) and CHCl3-MeOH (19/1). The titled compound was obtained as colorless crystals (148 mg, 61%).

Workup

  1. customThe mixture was quenched with 1 M HCl (5 mL)
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. washThe filtrate was washed with 50% K2CO3 aq.
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. dry with materialThe combined organic layer was dried (K2CO3)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. washthe column was eluted with CHCl3-acetone (9/1˜4/1) and CHCl3-MeOH (19/1)

Sources & evidence

ORD record
ord-b8c3f0a30131469785e1e7e3ef7d8f3b
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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