Methanol → HCID 22645387, compound

HRID 2414267Notes

Reaction equation

HRID 2414267 reaction equation
[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:27])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:14]=2)[CH:9]([CH3:28])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)CC)C.[CH3:36][OH:37].CN(C)[CH:40]=[O:41]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:27])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:36]([O:41][CH3:40])=[O:37])[CH:14]=2)[CH:9]([CH3:28])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 22645393HCID 22645393, compound

Product 1

HCID 22645387HCID 22645387, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 1-hexyl-3,4-dimethyl-4-(3-trifluoromethanesulfonyloxyphenyl)piperidine (Preparation 1, 500 mg, 1.19 mmol) in anhydrous N,N-dimethylformamide (6 mL) was added triethylamine (1.7 mL, 12.2 mmol) and anhydrous methanol (1.0 mL, 24.7 mmol). The solution was de-oxygenated by evacuating and flushing with nitrogen five times. Palladium(II) acetate (27 mg, 0.12 mmol) and 1,1 ′-bis(diphenylphosphino)ferrocene (67 mg, 0.12 mmol) were added and the mixture was de-oxygenated again, using the same procedure as before. Carbon monoxide gas was bubbled through the mixture for 5 minutes and it was then stirred under an atmosphere of carbon monoxide and heated at 120° C. overnight. The solvent was removed in vacuo to give a brown oil (0.7 g) which was purified by column chromatography on silica gel (35 g) eluted with a gradient of ethyl acetate:hexane:0.880 ammonia (10:190:1 to 10:90:1 to 25:75:1). This gave the title compound as a yellow oil (250 mg).

Workup

  1. customby evacuating
  2. customflushing with nitrogen five times
  3. customCarbon monoxide gas was bubbled through the mixture for 5 minutes
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f5c47deda0b442e1be0f8d5b309f7fd0
Source dataset
uspto-grants-2004_11
Patent number
US06812236B2

Reaction notes

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