Potassium Carbonate → HCID 59299412, compound

HRID 2235314Notes

Reaction equation

HRID 2235314 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11]C[N:9]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:8]2=[O:19])=[C:4]([Cl:22])[CH:3]=1.[OH:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.[Cu]I>[Cl:22][C:4]1[CH:3]=[C:2]([N:26]2[CH2:27][CH2:28][CH:24]([OH:23])[CH2:25]2)[CH:21]=[CH:20][C:5]=1[CH2:6][CH:7]1[CH2:12][CH2:11][N:9]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[C:8]1=[O:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 982104-HydroxypyrrolidineHCID 59299455HCID 59299455, compound

Product 1

HCID 59299412HCID 59299412, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31374DimethylacetamideSolvent

Procedure

Dissolve 3-(4-bromo-2-chloro-benzyl)-1-cyclohexyl-piperidin-2-one (Example 55) (0.2 g, 0.54 mmol), rac-3-hydroxy-pyrrolidine (0.053 mL, 0.64 mmol), copper (I) iodide (10.5 mg, 0.05 mmol), in dimethylacetamide (1 mL) with potassium carbonate (0.13 g, 0.95 mmol), and heat at 90° C. 48 h. Evaporate and purify the residue by chromatography on silica gel (eluting 10% to 100% ethyl acetate in hexane) to give the desired product (39 mg, 19%). MS (ES+) m/z=377 (M+H)+.

Workup

  1. custom48 h
  2. customEvaporate
  3. custompurify the residue by chromatography on silica gel (eluting 10% to 100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3a3cd54d32ca4b28b65b1c2af90cf717
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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