1,2,3,6-Tetrahydropyridine → HCID 23121941, compound

HRID 1713553Notes

Reaction equation

HRID 1713553 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([C:13]3[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=3)=[O:12])[CH2:10][CH:5]2[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:3]1.[NH:33]1[CH2:38][CH:37]=[CH:36][CH2:35][CH2:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.O>[N:33]1([CH2:17][C:16]2[CH:19]=[CH:20][C:13]([C:11]([N:9]3[CH2:8][CH2:7][N:6]4[C:2](=[O:1])[O:3][C:4]([C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=5)([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH:5]4[CH2:10]3)=[O:12])=[CH:14][CH:15]=2)[CH2:34][CH:35]=[CH:36][CH2:37][CH2:38]1

Participants

6

Reactant 3

HCID 127501,2,3,6-TetrahydropyridineHCID 5049666Sodium triacetoxyborohydrideHCID 23121964HCID 23121964, compound

Product 1

HCID 23121941HCID 23121941, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-7(1H)-yl)carbonyl]benzaldehyde (0.15 g, 0.35 mmol) and 1,2,3,6-tetrahydropyridine (44 mg, 0.53 mmol) in tetrahydrofuran (4 mL) was added sodium triacetoxyborohydride (0.11 g, 0.52 mmol), and the mixture was stirred at room temperature for 27 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 silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=4:1) and crystallized from diisopropyl ether to obtain the title compound (70 mg, yield 41%).

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 silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=4:1)
  7. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-d85c9d285a7845a39c75eb7751e1af77
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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