Imidazole → (4aR,5R,8aR)-5-[(R)-1,5-Dimethyl-5-trimethylsilanyloxy-hexyl]-4a-methyl-octahydro-naphtalen-1-one

HRID 1075558노트

반응식

HRID 1075558 반응식
[OH:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][CH2:5][C@H:6]([C@H:8]1[CH2:17][CH2:16][CH2:15][C@@H:14]2[C@:9]1([CH3:19])[CH2:10][CH2:11][CH2:12][C:13]2=[O:18])[CH3:7].[CH3:22][Si:23](C1NC=CN=1)([CH3:25])[CH3:24].C[Si](Cl)(C)C.N1C=CN=C1>O1CCCC1>[CH3:7][C@@H:6]([C@H:8]1[CH2:17][CH2:16][CH2:15][C@@H:14]2[C@:9]1([CH3:19])[CH2:10][CH2:11][CH2:12][C:13]2=[O:18])[CH2:5][CH2:4][CH2:3][C:2]([CH3:20])([O:1][Si:23]([CH3:25])([CH3:24])[CH3:22])[CH3:21]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 11022791(4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-octahydro-naphtalen-1-oneHCID 14420972TMS-Imidazole

생성물 1

HCID 70273562(4aR,5R,8aR)-5-[(R)-1,5-Dimethyl-5-trimethylsilanyloxy-hexyl]-4a-methyl-octahydro-naphtalen-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 24 mg (0.08 mMol) of (4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-octahydro-naphtalen-1-one in 0.5 ml of tetrahydrofuran is cooled under stirring and Argon atmosphere to 0°. The reaction mixture is stirred for an additional hour after addition of 12 μl (0.08 mMol) of trimethylsilylimidazole, of 5.1 μl (0.04 mMol) of trimethylsilylchloride and of 2.8 mg (0.04 mMol) of imidazole. The reaction mixture is poured into ice water, extracted three times with diethylether, the combined organic extracts are washed twice with brine and dried over Na2SO4. The organic solvent is evaporated in vacuo and the residue is chromatographed over 5 g of silicagel with hexane/diethylether 9/1 to yield 25 mg of pure, oily (4aR,5R,8aR)-5-[(R)-1,5-Dimethyl-5-trimethylsilanyloxy-hexyl]-4a-methyl -octahydro-naphtalen-1-one

후처리

  1. customto 0°
  2. stirringThe reaction mixture is stirred for an additional hour
  3. extractionextracted three times with diethylether
  4. washthe combined organic extracts are washed twice with brine
  5. dry with materialdried over Na2SO4
  6. customThe organic solvent is evaporated in vacuo
  7. customthe residue is chromatographed over 5 g of silicagel with hexane/diethylether 9/1

출처 및 근거

ORD 기록
ord-7e90d3077e4945459e8b3d1087ddc67b
출처 데이터셋
uspto-grants-1999_05
특허 번호
US05905074

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