Acetic Acid → HCID 44241966, compound

HRID 1808137Notes

Reaction equation

HRID 1808137 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([C:13]2[O:17][N:16]=[C:15]([CH3:18])[N:14]=2)[NH2:12])=[CH:2]1.[CH3:19][N:20]([CH3:34])[C:21]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O)(=O)C>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@@H:11]([NH:12][CH:24]2[CH2:23][CH2:22][C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([N:20]([CH3:34])[CH3:19])[CH2:26][CH2:25]2)[C:13]2[O:17][N:16]=[C:15]([CH3:18])[N:14]=2)=[CH:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24436Sodium SulfateHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneHCID 68795995HCID 68795995, compound

Product 1

HCID 44241966HCID 44241966, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-2-(1H-Indol-3-yl)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine (400 mg, 1.65 mmol) and 4-dimethylamino-4-phenylcyclohexanone (358.7 g, 1.65 mmol) in anhydrous tetrahydrofuran (50 mL) was mixed with sodium sulphate (1.1 g) and stirred for 2 h at room temperature. After adding acetic acid (248 mg, 4.1 mmol) sodium triacetoxyboron hydride (524 mg, 2.47 mmol) was added and the reaction mixture stirred for 16 h at room temperature. The solvent was removed in a vacuum, the residue mixed with 1M potassium carbonate solution (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phases were dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product was purified by flash chromatography (400 g, 20×5.6 cm) with ethyl acetate/isopropanol/triethylamine (10:0.3:0.01→5:1:0.1).

Workup

  1. additionwas added
  2. stirringthe reaction mixture stirred for 16 h at room temperature
  3. customThe solvent was removed in a vacuum
  4. additionthe residue mixed with 1M potassium carbonate solution (50 mL)
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. dry with materialThe combined organic phases were dried with sodium sulphate
  7. concentrationconcentrated to low volume in a vacuum
  8. customThe raw product was purified by flash chromatography (400 g, 20×5.6 cm) with ethyl acetate/isopropanol/triethylamine (10:0.3:0.01→5:1:0.1)

Sources & evidence

ORD record
ord-49161dacb9c4409680f572aa1af70268
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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