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Aluminium lithium hydride → 2-(2-(4-Chlorophenyl)-2,4,5,6-tetrahydrocyclopenta[C]pyrazol-3-YL)-2-cyclohexylethanol

HRID 889372
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인쇄 미리보기

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HRID 889372 반응식
C([O:3][C:4](=O)[CH:5]([C:12]1[N:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:14]=[C:15]2[CH2:19][CH2:18][CH2:17][C:16]=12)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([N:13]2[C:12]([CH:5]([CH:6]3[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]3)[CH2:4][OH:3])=[C:16]3[CH2:17][CH2:18][CH2:19][C:15]3=[N:14]2)=[CH:25][CH:24]=1
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참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 67387258[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid ethyl ester

생성물 1

HCID 673874592-(2-(4-Chlorophenyl)-2,4,5,6-tetrahydrocyclopenta[C]pyrazol-3-YL)-2-cyclohexylethanol수율 80.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

A solution of [2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid ethyl ester (500 mg, 1.2 mmol) in THF (25 ml) was added within 20 min to an ice cold suspension of lithium aluminium hydride (66 mg, 1.7 mmol) in THF (25 ml). The solution was stirred at 0° C. for 45 min, filtered over Speedex and the filtrate was brought to dryness under reduced pressure. The residue was taken up in ice water/brine 1/1 and iPrOAc. The layers were separated and the aqueous layer was extracted one more time with iPrOAc. The combined extracts were dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give the title compound (336 mg, 0.97 mmol; 79%) as yellow oil which was used in the next step without further purification. MS: m/e=345.2 [M+H+].

후처리

  1. filtrationfiltered over Speedex
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted one more time with iPrOAc
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure

출처 및 근거

ORD 기록
ord-2e62b7990462425f9e89ab41b7aa9e57
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08252826B2

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