Ethyl Acetate → HCID 178484147, compound

HRID 1159358Notes

Reaction equation

HRID 1159358 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].CS([O:11][C@H:12]1[CH2:15][C@@H:14]([CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH3:18])[CH2:13]1)(=O)=O.CCO[C:29]([CH3:31])=O>CS(C)=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:18][N:17]([CH2:16][C@H:14]1[CH2:15][C@H:12]([O:11][C:12]2[CH:15]=[CH:3][C:2]([CH2:5][N:17]3[CH2:31][CH2:29][CH2:14][CH2:16]3)=[CH:1][CH:13]=2)[CH2:13]1)[C:19](=[O:20])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 178484154HCID 178484154, compound

Product 1

HCID 178484147HCID 178484147, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution on intermediate 1,4-(pyrrolidin-1-ylmethyl)phenol (5.5 g, 62 mmol) and potassium tert-butoxide (3.5 g, 31 mmol) in DMSO (100 mL) was heated to 100° C. under vigorous stirring in a flow of argon. The mixture was stirred at this temperature for 15 min. A solution of compound 8 (4.5 g, 15.5 mmol) in DMSO (100 mL) and tetrabutylammonium bromide (1.5 g, 9 mmol) were added. The mixture was stirred at 100° C. for 1 h and cooled. The residue was dissolved in EtOAc (200 mL). The solution was washed with water (300 mL), 1 N NaOH (2×100 mL), brine, dried with Na2SO4, and evaporated. The residue was purified by chromatography (silica gel, 63/100 μm, 60 g, CHCl3/hexane 20:80→100:0, CHCl3/MeOH 100:0→80:20 to furnish the title compound (5.56 g, 96%). 1H NMR-data (DMSO-d6): 7.17 (d, 2H, Ph, J=8.6); 6.73 (d, 2H, Ph, J=8.6); 4.68-4.85 (m, 1H); 3.47 (s, 2H, CH2); 3.33 (d, 2H, CH2, J=7.8); 2.78 (s, 3H, NCH3); 2.50-2.60 (m, 1H); 2.33-2.44 (m, 4H); 2.00-2.27 (m, 4H); 1.62-1.71 (m, 4H); 1.38 (s, 9H, Boc).

Workup

  1. stirringThe mixture was stirred at this temperature for 15 min
  2. stirringThe mixture was stirred at 100° C. for 1 h
  3. temperaturecooled
  4. washThe solution was washed with water (300 mL), 1 N NaOH (2×100 mL), brine
  5. dry with materialdried with Na2SO4
  6. customevaporated
  7. customThe residue was purified by chromatography (silica gel, 63/100 μm, 60 g, CHCl3/hexane 20:80→100:0, CHCl3/MeOH 100:0→80:20

Sources & evidence

ORD record
ord-f5363bff515e40a984b549c5f7688850
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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