Methyl iodide → (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethyl-cyclopentanecarboxylic acid ethyl ester

HRID 1367504

反応式

HRID 1367504 の反応式
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:8][C@H:7]1[CH2:19][OH:20])=[O:5])[CH3:2].I[CH3:22]>[Ag]=O>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([O:11][Si:12]([C:15]([CH3:16])([CH3:18])[CH3:17])([CH3:13])[CH3:14])[CH2:8][C@H:7]1[CH2:19][O:20][CH3:22])=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 6328Methyl iodideHCID 59619451(1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclopentanecarboxylic acid ethyl ester

生成物 1

HCID 66918779(1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethyl-cyclopentanecarboxylic acid ethyl ester収率 43%

試薬・触媒・溶媒 1

HCID 92152Silver(II) oxide触媒

実験手順

To a solution of (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclopentanecarboxylic acid ethyl ester (Example 68/69 step 4, epimeric mixture, 509 mg) in iodomethane (24 g) was added silver oxide (3.9 g) in several portions over 8 days. After 12 days at room temperature, the reaction mixture was concentrated in vacuo, diluted with dichloromethane, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/EtOAc (1:0 to 9:1 v/v) as eluant to afford the title compound (228 mg, 43%) as light yellow oil. MS (EI): 317.1 (M+H)+.

後処理

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with dichloromethane
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/EtOAc (1:0 to 9:1 v/v) as eluant

出典と根拠

ORDレコード
ord-bd4a922d77d947ea9da40398bae20711
出典データセット
uspto-grants-2011_02
特許番号
US07893099B2

関連ノート

読み込み中…