Potassium Carbonate → (R)-N-(3-(tert-butyldimethylsilyloxy)-4-chlorobenzyl)-1-(3-chlorophenyl)ethanamine

HRID 1801602Notes

Reaction equation

HRID 1801602 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:17])=[C:7]([CH:16]=1)[O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[Cl:24][C:25]1[CH:26]=[C:27]([C@H:31]([NH2:33])[CH3:32])[CH:28]=[CH:29][CH:30]=1>CN(C=O)C.O.CCOCC>[Si:9]([O:8][C:7]1[CH:16]=[C:3]([CH:4]=[CH:5][C:6]=1[Cl:17])[CH2:2][NH:33][C@@H:31]([C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([Cl:24])[CH:26]=1)[CH3:32])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2507697(R)-1-(3-chlorophenyl)ethanamineHCID 59803153(5-(Bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane

Product 1

HCID 59803157(R)-N-(3-(tert-butyldimethylsilyloxy)-4-chlorobenzyl)-1-(3-chlorophenyl)ethanamineYield 50.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (5-(bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane 81 (1.00 g, 2.98 mmol) and potassium carbonate (0.453 g, 3.28 mmol) in DMF was stirred at room temp under N2. (R)-1-(3-Chlorophenyl)ethanamine (0.464 g, 2.98 mmol) was added to the solution and the reaction was stirred at room temperature for 8 h. The reaction was checked by TLC for completion. The reaction mixture was diluted with water and ether. The ether solution was washed with water (2×) and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography using a 5% to 30% gradient of EtOAc in hexanes as the eluant. The desired fractions were combined and concentrated to give (R)—N-(3-(tert-butyldimethylsilyloxy)-4-chlorobenzyl)-1-(3-chlorophenyl)ethanamine 82 (0.612 g, 50.1% yield) as a colorless oil. The product was carried forth to the next step without further purification.

Workup

  1. washThe ether solution was washed with water (2×) and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel chromatography
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d20668c43fd344b78a780a5811fc7c0e
Source dataset
uspto-grants-2013_01
Patent number
US08349831B2

Reaction notes

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