Triphenylphosphine → HCID 86709483, compound

HRID 1848472Notes

Reaction equation

HRID 1848472 reaction equation
[CH3:1][N:2]1[CH2:9][C@H:8]2[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:4]([CH2:5][C:6](OS(C(F)(F)F)(=O)=O)=[CH:7]2)[CH2:3]1.C(N(C(C)C)CC)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][N:2]1[CH2:9][C@H:8]2[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:4]([CH2:5][C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7]2)[CH2:3]1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 86709481HCID 86709481, compound

Product 1

HCID 86709483HCID 86709483, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (1R,5S)-tert-butyl 3-methyl-7-(((trifluoromethyl)sulfonyl)oxy)-3,9-diazabicyclo[3.3.1]non-6-ene-9-carboxylate (14 g, 36 mmol) and diisopropylethylamine (9.47 mL, 54.3 mmol) in methanol (100 mL) and DMF (100 mL) was triphenylphosphine (0.95 g, 3.62 mmol) and palladium (II) acetate (0.407 g, 1.81 mmol). The mixture was stirred under carbon monoxide atmosphere for 24 h. The mixture was concentrated and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, concentrated and the residue was purified on silica gel using ethyl acetate and hexane as eluting solvents to give the title compound. LC/MS: (M+1)+: 297.2.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue was purified on silica gel
  7. washas eluting solvents

Sources & evidence

ORD record
ord-1561931860654e55985c085326340479
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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