Acetic Acid → HCID 23121851, compound

HRID 1713513Notes

Reaction equation

HRID 1713513 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[CH2:27]([N:34]1[CH2:39][CH2:38][C:37](=O)[CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.O>[C:17]1([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:11]3[CH2:12][N:13]([CH:37]4[CH2:36][CH2:35][N:34]([CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH2:39][CH2:38]4)[CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 192201-Benzyl-4-piperidone2×HCID 5049666Sodium triacetoxyborohydride2×HCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121851HCID 23121851, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.15 g, 0.51 mmol), acetic acid (0.045 mL, 0.79 mmol) and 1-benzyl-4-piperidone (0.12 g, 0.63 mmol) in tetrahydrofuran (5 mL) was added sodium triacetoxyborohydride (0.16 g, 0.75 mmol), and the mixture was stirred at room temperature for 16 hours. 1-Benzyl-4-piperidone (0.060 mL) and sodium triacetoxyborohydride (0.16 g) were added thereto, and the mixture was stirred at room temperature for 3 days. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, water and saturated brine, and then 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=98:2 to hexane:ethyl acetate=1:1) and recrystallized from ethyl acetate-hexane to obtain the title compound (70 mg, yield 29%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 days
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solid was filtered off
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified with amino silica gel column chromatography (hexane:ethyl acetate=98:2 to hexane:ethyl acetate=1:1)
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-52c526255b274adc9b48c810a7181162
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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