Imidazole → (-)-(1R,2S)-2-phenyl-1-cyclohexyl hydroxyacetate

HRID 487369

反応式

HRID 487369 の反応式
C([O:8][CH2:9][C:10](Cl)=[O:11])C1C=CC=CC=1.[C:13]1([C@@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]2[OH:25])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([Si](Cl)(C(C)C)C(C)C)(C)C.N1C=CN=C1>CN(C)C=O.CCCCC>[OH:11][CH2:10][C:9]([O:25][C@@H:20]1[CH2:21][CH2:22][CH2:23][CH2:24][C@H:19]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8]

参加物

7

反応物 4

HCID 795ImidazoleHCID 102793rel-(1R,2S)-2-PhenylcyclohexanolHCID 139400Triisopropylsilyl chlorideHCID 177085Benzyloxyacetyl chloride

生成物 1

HCID 10059921(-)-(1R,2S)-2-phenyl-1-cyclohexyl hydroxyacetate収率 95%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8003Pentane溶媒

実験手順

To obtain 1c(-), a solution of (-)-(1R,2S)-2-phenyl-1-cyclohexyl hydroxyacetate (851 mg, 3.63 mmol) was prepared through esterification of benzyloxyacetyl chloride with (-)-(1R,2S)-2-phenyl-1-cyclohexanol followed by hydrogenolysis. Then, triisopropylsilyl chloride (840 mg, 4.36 mmol) and imidazole (618 mg, 9.08 mmol) in dimethylformamide (DMF) (1.7 mL) was stirred at room temperature for 12-20 hours. The mixture was poured into pentane (25 mL), and washed with water and brine. The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was subjected to a purification on a short silica gel column using hexane/chloroform (3/1) as the eluant to give pure 1c(-) (1.35 g, 95% yield) as a colorless oil.

後処理

  1. customTo obtain 1c(-)
  2. washwashed with water and brine
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was subjected to a purification on a short silica gel column
  6. customto give pure 1c(-) (1.35 g, 95% yield) as a colorless oil

出典と根拠

ORDレコード
ord-8c8b239c359f4197a5536012d4027c08
出典データセット
uspto-grants-1994_03
特許番号
US05294737

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