Acetaldehyde → HCID 23121849, compound

HRID 1713564Notes

Reaction equation

HRID 1713564 reaction equation
[ClH:1].[CH:2]1([NH:5][CH2:6][CH2:7][NH:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]3[C:17](=[O:32])[O:18][C:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:13]3[CH2:12]2)=[O:10])[CH2:4][CH2:3]1.[CH2:33](N(CC)CC)[CH3:34].C(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[ClH:1].[CH:2]1([N:5]([CH2:33][CH3:34])[CH2:6][CH2:7][NH:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]3[C:17](=[O:32])[O:18][C:19]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:13]3[CH2:12]2)=[O:10])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 23121921HCID 23121921, compound

Product 1

HCID 23121849HCID 23121849, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of N-[2-(cyclopropylamino)ethyl]-tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamide hydrochloride (0.15 g, 0.33 mmol), triethylamine (67 mg, 0.66 mmol) and 90% acetaldehyde (0.040 mL, 0.64 mmol) in 1,2-dichloroethane (5 mL) was added sodium triacetoxyborohydride (0.14 g, 0.66 mmol), and the mixture was stirred at room temperature for 13 hours. The reaction solution was diluted with water and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated. The residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate) and concentrated. A 4 M hydrogen chloride/ethyl acetate solution (5 mL) was added thereto, and then concentrated. The residue was crystallized from diethyl ether to obtain the title compound (54 mg, yield 34%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe solid was filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate)
  7. concentrationconcentrated
  8. additionA 4 M hydrogen chloride/ethyl acetate solution (5 mL) was added
  9. concentrationconcentrated
  10. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-265d7dd1e63945c0b464ab9de5542b7d
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

Loading…