Triphenylphosphine → 4-{2-[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethoxy}-3,5-dimethyl-benzoic acid methyl ester

HRID 889373Notes

Reaction equation

HRID 889373 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:14][OH:15])=[C:11]3[CH2:22][CH2:23][CH2:24][C:10]3=[N:9]2)=[CH:4][CH:3]=1.[CH3:25][O:26][C:27](=[O:37])[C:28]1[CH:33]=[C:32]([CH3:34])[C:31](O)=[C:30]([CH3:36])[CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH3:25][O:26][C:27](=[O:37])[C:28]1[CH:29]=[C:30]([CH3:36])[C:31]([O:15][CH2:14][CH:13]([C:12]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]=[C:10]3[CH2:24][CH2:23][CH2:22][C:11]=23)[CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:32]([CH3:34])[CH:33]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 12389264Methyl 4-hydroxy-3,5-dimethylbenzoateHCID 673874592-(2-(4-Chlorophenyl)-2,4,5,6-tetrahydrocyclopenta[C]pyrazol-3-YL)-2-cyclohexylethanol

Product 1

HCID 533902524-{2-[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethoxy}-3,5-dimethyl-benzoic acid methyl esterYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethanol (100 mg, 290 umol) in THF (2 ml) was added 4-hydroxy-3,5-dimethyl-benzoic acid methyl ester (57 mg, 319 umol; CAS Reg. No. 34137-14-9) and tri-phenylphosphine (91 mg, 348 umol) at ambient temperature under an argon atmosphere. The mixture was cooled to 0° C., di-tert-butyl azodicarboxylate (80 mg, 348 umol) was added and the suspension was stirred for 48 h at ambient temperature. The solvent was removed under reduced pressure to give a solid which was purified by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water to obtain the title compound (19 mg, 37 umol; 13%) as yellow solid. MS: m/e=507.2 [M+H+].

Workup

  1. customat ambient temperature
  2. customThe solvent was removed under reduced pressure
  3. customto give a solid which
  4. customwas purified by preparative HPLC on reversed phase
  5. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-dc0e3942efd8458890a64e496c292b6f
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

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