Acetone → HCID 56836235, compound

HRID 591209Notes

Reaction equation

HRID 591209 reaction equation
[CH2:1]([C:8]1([C:13]2[CH:14]=[C:15]([CH:29]=[CH:30][CH:31]=2)[O:16][CH2:17][CH2:18][NH:19][S:20]([C:23]2[N:24]=[CH:25][N:26]([CH3:28])[CH:27]=2)(=[O:22])=[O:21])[CH2:12][CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][C:33]([CH3:35])=O.[O-]S([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCl.C(O)(=O)C>[CH2:1]([C:8]1([C:13]2[CH:14]=[C:15]([CH:29]=[CH:30][CH:31]=2)[O:16][CH2:17][CH2:18][NH:19][S:20]([C:23]2[N:24]=[CH:25][N:26]([CH3:28])[CH:27]=2)(=[O:22])=[O:21])[CH2:12][CH2:11][N:10]([CH:33]([CH3:35])[CH3:32])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 180AcetoneHCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 56836035HCID 56836035, compound

Product 1

HCID 56836235HCID 56836235, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methyl-1H-imidazole-4-sulfonic acid {2-[3-(3-benzyl-pyrrolidin-3-yl)phenoxy]-ethyl}-amide (example 61, 59 mg, 0.13 mmol) in dichloromethane under nitrogen was added acetone (8 mg, 0.14 mmol), two drops acetic acid, 2 mg Na2SO4, sodium triacetoxyborohydride. The mixture was stirred over night at room temperature. Saturated NaHCO3-solution was added and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried over Na2SO4 and the solvent evaporated affording 54 mg of colorless oil. Purification on 4 g SiO2 with dichloromethane+5% MeOH to 10% MeOH afforded 4 mg of product.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-fc87b2055a7146418433280b3638c0ae
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

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