Tributylphosphine → HCID 58629852, compound

HRID 1391766Notes

Reaction equation

HRID 1391766 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.O[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])=[O:34])=[CH:26][CH:25]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.P(CCCC)(CCCC)CCCC>C1COCC1>[F:22][C:2]([F:21])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([CH:15]([O:20][C:24]3[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])=[O:34])=[CH:28][CH:29]=3)[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 58629819HCID 58629819, compoundHCID 586298221-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol

Product 1

HCID 58629852HCID 58629852, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol (62 mg, 0.20 mmol) and 2-(trimethylsilyl)ethyl 4-(4-hydroxyphenyl)butanoate (55 mg, 0.20 mmol) in dry THF (4 mL) at 0° C. (ice/water bath), under nitrogen, was added ADDP (102 mg, 0.40 mmol) followed by nBu3P (100 μL, 0.40 mmol), and the mixture stirred with slow warming to rt over 64.5 hours. The mixture was then concentrated under vacuum and the solid residue partitioned between DCM (5 mL) and water (5 mL) using a hydrophobic frit. The layers were separated and the aqueous layer re-extracted with DCM (5 mL) and the combined organic layer reduced. Purification by SPE (silica, 5 g Cartridge) eluting with cyclohexane:EtOAc (gradient 50:1 to 7.5:1) afforded the title compound (42 mg).

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. customthe solid residue partitioned between DCM (5 mL) and water (5 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer re-extracted with DCM (5 mL)
  5. customPurification by SPE (silica, 5 g Cartridge)
  6. washeluting with cyclohexane

Sources & evidence

ORD record
ord-5cd6a0c76808416eb38ff0fd6e549771
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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