Potassium Phosphate, Tribasic → HCID 57586421, compound

HRID 2190340Notes

Reaction equation

HRID 2190340 reaction equation
N1CCC[C@H]1C(O)=O.Br[C:10]1[CH:25]=[CH:24][C:13]([CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:12][CH:11]=1.[C:26]1([CH:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:33][CH2:34][NH2:35])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CCOC(C)=O.[Cu]I.CS(C)=O>[Si:17]([O:16][CH2:15][CH2:14][C:13]1[CH:24]=[CH:25][C:10]([NH:35][CH2:34][CH2:33][CH:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:11][CH:12]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 796983,3-DiphenylpropylamineHCID 145742L-ProlineHCID 23254500[2-(4-Bromophenyl)ethoxy](tert-butyl)dimethylsilane

Product 1

HCID 57586421HCID 57586421, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of copper(I) iodide (0.195 g, 1.02 mmol), (S)-pyrrolidine-2-carboxylic acid (0.223 g, 1.94 mmol), (4-bromophenethoxy)(tert-butyl)dimethylsilane, prepared in the previous step, and 3,3-diphenylpropan-1-amine (3.16 g, 15.0 mmol) was added potassium phosphate (4.27 g, 20.1 mmol), and DMSO (16 mL). The reaction mixture was heated to 90° C. for 1 d and diluted with EtOAc. The organic phase was washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 5% to 15% EtOAc in hexanes) gave 4-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(3,3-diphenylpropyl)benzenamine 66.

Workup

  1. washThe organic phase was washed with water (1×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (eluted with 5% to 15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bbcab78cdf044d6195fcaf80384c4977
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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