Potassium trimethylsilanolate → (1R)-2-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 901588ノート

反応式

HRID 901588 の反応式
[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:3]=1[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][C@@H:18]([C:20]2[CH:31]=[CH:30][C:23]3[O:24][C:25]([CH3:29])([CH3:28])[O:26][CH2:27][C:22]=3[CH:21]=2)[O:17]C1=O.C[Si](C)(C)[O-].[K+]>C1COCC1>[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:3]=1[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:19][C@@H:18]([C:20]1[CH:31]=[CH:30][C:23]2[O:24][C:25]([CH3:28])([CH3:29])[O:26][CH2:27][C:22]=2[CH:21]=1)[OH:17]

参加物

4

反応物 2

HCID 23668039Potassium trimethylsilanolateHCID 46833391(5R)-3-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

生成物 1

HCID 46834265(1R)-2-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol収率 97.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (5R)-3-(6-{2-[(2,6-dichlorobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (140 mg) in THF (7 ml) under nitrogen was treated with potassium trimethylsilanolate (130 mg) and the mixture was heated (oil bath temperature 80°) with stirring for 3 h. The mixture was cooled to 20° and was partitioned between phosphate buffer solution (20 ml, pH6.5) and EtOAc (20 ml). The organic phase was separated, dried (NaSO4) and the solvent evaporated in vacuo to give the title compound (130 mg). LCMS RT=3.00 min.

後処理

  1. temperaturethe mixture was heated (oil bath temperature 80°)
  2. temperatureThe mixture was cooled to 20°
  3. customwas partitioned between phosphate buffer solution (20 ml, pH6.5) and EtOAc (20 ml)
  4. customThe organic phase was separated
  5. dry with materialdried (NaSO4)
  6. customthe solvent evaporated in vacuo

出典と根拠

ORDレコード
ord-15a056f0184a4df2a9520538d683b649
出典データセット
uspto-grants-2008_04
特許番号
US07361787B2

反応ノート

読み込み中…