Triphenylphosphine → HCID 178520986, compound

HRID 1984016Notes

Reaction equation

HRID 1984016 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11]([C@H:13]3[CH2:18][CH2:17][C@@H:16]([OH:19])[CH2:15][CH2:14]3)=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[N:20]1([C:25]2[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=2)[CH:24]=[N:23][CH:22]=[N:21]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>[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11]([C@H:13]3[CH2:18][CH2:17][C@H:16]([O:19][C:28]4[CH:29]=[CH:30][C:25]([N:20]5[CH:24]=[N:23][CH:22]=[N:21]5)=[CH:26][CH:27]=4)[CH2:15][CH2:14]3)=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 1100644-(1,2,4-Triazol-1-yl)phenolHCID 178520989HCID 178520989, compound

Product 1

HCID 178520986HCID 178520986, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 200 mg (0.75 mmol) of cis-(4-cyclobutyl-piperazin-1-yl)-(4-hydroxy-cyclohexyl)-methanone, 133 mg (0.83 mmol) of 4-(1,2,4-triazole-1-yl)phenol, 241 mg (0.92 mmol) of triphenylphosphine in 1.5 ml of THF, a mixture of 212 mg (0.92 mmol) of di-tert-butyl azodicarboxylate in 1.5 ml of THF was added dropwise at 0° C., and stirred for 72 h at room temperature. After evaporation, the residue was purified by column chromatography on silica gel elating with CH2Cl2 and methanol=from 99:1 to 9:1. After that, the residue was purified by column chromatography on NH2-coating silica gel eluting % with CH2Cl2 and ethyl acetate=from 100:0 to 99:2. The combined product fractions were evaporated to dryness to yield 35 mg (11%) of the title compound. MS (m/e): 410.3 (MH+).

Workup

  1. additionwas added dropwise at 0° C.
  2. customAfter evaporation
  3. customthe residue was purified by column chromatography on silica gel elating with CH2Cl2 and methanol=from 99:1 to 9:1
  4. customAfter that, the residue was purified by column chromatography on NH2-coating silica gel eluting % with CH2Cl2 and ethyl acetate=from 100:0 to 99:2
  5. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-bc8a763cdc32423c8daa29543a35e5a2
Source dataset
uspto-grants-2009_06
Patent number
US07544683B2

Reaction notes

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