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

HRID 889372
Notes
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Reaction equation

HRID 889372 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

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+].

Workup

  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

Sources & evidence

ORD record
ord-2e62b7990462425f9e89ab41b7aa9e57
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08252826B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes