Triphenylphosphine → 4-[4-(5-Cyclohexylcarbamoyl-3-methylpyrazol-1-yl)phenoxy]piperidine-1-carboxylic acid tert-butyl ester

HRID 1013034Notes

Reaction equation

HRID 1013034 reaction equation
[CH:1]1([NH:7][C:8]([C:10]2[N:11]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[N:12]=[C:13]([CH3:15])[CH:14]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42]([O:46][C:47]([N:49]1[CH2:54][CH2:53][CH:52](O)[CH2:51][CH2:50]1)=[O:48])([CH3:45])([CH3:44])[CH3:43].CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[C:42]([O:46][C:47]([N:49]1[CH2:54][CH2:53][CH:52]([O:22][C:19]2[CH:20]=[CH:21][C:16]([N:11]3[C:10]([C:8](=[O:9])[NH:7][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:14][C:13]([CH3:15])=[N:12]3)=[CH:17][CH:18]=2)[CH2:51][CH2:50]1)=[O:48])([CH3:45])([CH3:43])[CH3:44]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 582568112-(4-Hydroxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid cyclohexylamide

Product 1

HCID 589487744-[4-(5-Cyclohexylcarbamoyl-3-methylpyrazol-1-yl)phenoxy]piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-hydroxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid cyclohexylamide (300 mg, 1.00 mmol) and triphenylphosphine (291 mg, 1.11 mmol) in tetrahydrofuran (5 mL) was added 1-tert-butoxycarbonyl-4-hydroxypiperidine (221 mg, 1.10 mmol) followed by dropwise addition of diisopropylazodicarboxylate (216 μL, 1.10 mmol). The solution was stirred at room temperature overnight, concentrated and dissolved in ethyl acetate. The ethyl acetate was washed with water, dried (MgSO4) and concentrated to give the crude product in quantitative yield. LC-MS (C27H38N4O4 calculated 482) m/z 483 (M+H).

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in ethyl acetate
  3. washThe ethyl acetate was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-36330e5118a346319ebce1cc2cc1a891
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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