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

HRID 487369

반응식

HRID 487369 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8003Pentane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8c8b239c359f4197a5536012d4027c08
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05294737

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