Imidazole → 4-(Tert-butyldimethylsilyloxy)-2-ethylcyclopentanecarboxylic acid

HRID 1969915ノート

反応式

HRID 1969915 の反応式
[CH2:1]([C@@H:3]1[CH2:7][C@@H:6]([OH:8])[CH2:5][C@@H:4]1[C:9]([OH:11])=[O:10])[CH3:2].[CH3:12][C:13]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>CN(C=O)C.[Si](O[C@H]1C[C@H](C(O)=O)[C@H](CC)C1)(C(C)(C)C)(C)C>[Si:16]([O:8][CH:6]1[CH2:5][CH:4]([C:9]([OH:11])=[O:10])[CH:3]([CH2:1][CH3:2])[CH2:7]1)([C:13]([CH3:15])([CH3:14])[CH3:12])([CH3:18])[CH3:17]

参加物

6

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67997857HCID 67997857、化合物

生成物 1

HCID 585570834-(Tert-butyldimethylsilyloxy)-2-ethylcyclopentanecarboxylic acid

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 67998141(1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-ethylcyclopentanecarboxylic acid溶媒

実験手順

To a scalemic mixture enriched in (1S,2R,4R)-2-ethyl-4-hydroxycyclopentanecarboxylic acid (2.56 g, 16.21 mmol) in DMF (10.81 mL) was added TBDMSCl (2.93 g, 19.45 mmol) and imidazole (2.76 g, 40.5 mmol). The reaction mixture was stirred at ambient temperature for about 2 days then extracted with pentane (3×25 mL). The combined pentane layers were washed with water (25 mL) and brine (25 mL), dried over anhydrous MgSO4, filtered and concd under reduced pressure. The residue was purified using silica gel chromatography eluting with 20-100% EtOAc in heptane give a scalemic mixture enriched in (1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-ethylcyclopentanecarboxylic acid (1.13 g, 26%): LC/MS (Table 1, Method b) Rt=3.03 min; MS m/z: 273 (M+H)+.

後処理

  1. extractionthen extracted with pentane (3×25 mL)
  2. washThe combined pentane layers were washed with water (25 mL) and brine (25 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe residue was purified
  6. washeluting with 20-100% EtOAc in heptane
  7. customgive a scalemic mixture

出典と根拠

ORDレコード
ord-f3feaecbb5e041ea8c4855a137f93729
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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