N,N-Dimethylglycine → HCID 57864752, compound

HRID 2425535Notes

Reaction equation

HRID 2425535 reaction equation
[CH:1]([N:14]1[CH2:18][C@@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2Br)[C@H:16]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[OH:33])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O>O1CCOCC1.[Cu]I>[Cl:32][C:30]1[CH:29]=[CH:28][C:27]2[O:33][C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C@H:17]3[CH2:18][N:14]([CH:1]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:15][C@@H:16]3[C:26]=2[CH:31]=1

Participants

6

Reactant 3

HCID 673N,N-DimethylglycineHCID 10796Cesium carbonateHCID 67243930HCID 67243930, compound

Product 1

HCID 57864752HCID 57864752, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of trans-2-(1-benzhydryl-4-(2-bromophenyl)pyrrolidin-3-yl)-4-chlorophenol (1.0 g, 1.93 mmol), cesium carbonate (1.26 g, 3.85 mmol, 2.0 eq.), N,N-dimethylglycine (79.5 mg, 0.77 mmol, 0.4 eq.) and CuI (147 mg, 0.77 mmol, 0.4 eq.) in dioxane (10 ml) was heated to reflux overnight while stirring under inert nitrogen atmosphere. The reaction mixture was filtered over Celite on a glass filter. The residual solids were washed with dioxane (15 ml). The combined filtrates were concentrated under vacuum to give the title compound as an oil, 0.9 g in quantitative yield. The purity according to LC-MS was 72%. The product was used without further purification. MS: M+1=437, 439 found. 1H-NMR (CDCl3) δ (ppm) 3.01-3.20 4H, m; 3.65 2H, m; 4.61 1H, m; 6.93-7.55 17H, m, ArH.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationThe reaction mixture was filtered over Celite on a glass
  4. filtrationfilter
  5. washThe residual solids were washed with dioxane (15 ml)
  6. concentrationThe combined filtrates were concentrated under vacuum

Sources & evidence

ORD record
ord-472160bc2949457fbc488c25bb932536
Source dataset
uspto-grants-2011_06
Patent number
US07964739B2

Reaction notes

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