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

HRID 1801602ノート

反応式

HRID 1801602 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d20668c43fd344b78a780a5811fc7c0e
出典データセット
uspto-grants-2013_01
特許番号
US08349831B2

反応ノート

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