Imidazole → (1S,3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanol

HRID 1677941ノート

反応式

HRID 1677941 の反応式
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4]1.N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C=O)C>[Si:14]([O:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride2 回HCID 586511153-(Hydroxymethyl)cyclopentanol

生成物 1

HCID 66797963(1S,3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanol収率 31%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (1S,3S)-3-(hydroxymethyl)cyclopentanol (453.0 mg, 0.003276 mol) and 1H-imidazole (669 mg, 0.00983 mol) in DMF (35.8 mL) under an atmosphere of nitrogen was added tert-butyldimethylsilyl chloride (494 mg, 0.00328 mol). The mixture was stirred for 1.25 hours, then tert-butyldimethylsilyl chloride (49 mg, 0.00033 mol) was added. After an additional hour of stirring, the reaction was quenched with water, extracted with ethyl acetate (3×), dried with anhydrous Na2SO4, filtered, and concentrated. The residue was filtered through a plug of silica with 30% EtOAc/hexanes to obtain 234.1 mg (31%) of the title compound.

後処理

  1. stirringAfter an additional hour of stirring
  2. customthe reaction was quenched with water
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationThe residue was filtered through a plug of silica with 30% EtOAc/hexanes

出典と根拠

ORDレコード
ord-ce3c0f8818d44e0c92ed64ebf8c21344
出典データセット
uspto-grants-2011_08
特許番号
US08008307B2

反応ノート

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