Triphenylphosphine → HCID 178453648, compound

HRID 1486478Notes

Reaction equation

HRID 1486478 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[OH:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:46]([O:50][C:51](=[O:61])[NH:52][CH2:53][C@H:54]1[CH2:59][CH2:58][C@@H:57](O)[CH2:56][CH2:55]1)([CH3:49])([CH3:48])[CH3:47]>O1CCCC1.O>[C:46]([O:50][C:51](=[O:61])[NH:52][CH2:53][C@H:54]1[CH2:55][CH2:56][C@H:57]([O:12][C:7]2[C:6]3[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=3)[N:10]=[CH:9][CH:8]=2)[CH2:58][CH2:59]1)([CH3:49])([CH3:47])[CH3:48]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178453649HCID 178453649, compoundHCID 178516458HCID 178516458, compound

Product 1

HCID 178453648HCID 178453648, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

8-Fluoroquinolin-4-ol (948 mg, 5.81 mmol), triphenylphosphine (1.52 g, 5.81 mmol) and DIAD (1.17 g, 5.81 mmol) were dissolved in tetrahydrofuran (140 mL). After adding tert-butyl-N-[(cis-4-hydroxycyclohexyl)methyl]carbamate (1.11 g, 4.84 mmol), the reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, extracted with ethyl acetate and the combined organic phases were dried over sodium sulphate. After removal of the solvent residues and chromatographic purification of the residue, the product was obtained at 42% yield (960 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined organic phases were dried over sodium sulphate
  3. customAfter removal of the solvent residues and chromatographic purification of the residue
  4. customthe product was obtained at 42% yield (960 mg)

Sources & evidence

ORD record
ord-9380352d0a4c4da381bf77c0de49563d
Source dataset
uspto-grants-2016_08
Patent number
US09428460B2

Reaction notes

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