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

HRID 1969915노트

반응식

HRID 1969915 반응식
[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]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67997857HCID 67997857, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 67998141(1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-ethylcyclopentanecarboxylic acid용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-f3feaecbb5e041ea8c4855a137f93729
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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