Trimethylsilyl iodide → HCID 86592008, compound

HRID 1785874Notes

Reaction equation

HRID 1785874 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C@H:23]([N:30]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:31](=[O:34])[CH2:32][CH3:33])[CH2:22][C@@H:21]3[CH3:41])=[O:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=O)C.I[Si](C)(C)C>C(#N)C>[CH3:41][C@H:21]1[CH2:22][C@@H:23]([N:30]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:31](=[O:34])[CH2:32][CH3:33])[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:20]1[C:18](=[O:19])[C:15]1[CH:14]=[CH:13][C:12]([CH:9]2[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86592009HCID 86592009, compound2×

Product 1

HCID 86592008HCID 86592008, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(±)-Cis-N-[2-methyl-1-(4-piperidin-4-yl-benzoyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-N-phenyl-propionamide was prepared from (±)-cis-4-{4-[2-methyl-4-(phenyl-propionyl-amino)-3,4-dihydro-2H-quinoline-1-carbonyl]-phenyl}-piperidine-1-carboxylic acid ethyl ester. (±)-Cis-4-{4-[2-methyl-4-(phenyl-propionyl-amino)-3,4-dihydro-2H-quinoline-1-carbonyl]-phenyl}-piperidine-1-carboxylic acid ethyl ester (96 mg, 0.17 mmol) was dissolved in acetonitrile (2 mL). Iodotrimetylsilane (74 uL, 0.51 mmol) was added and the reaction was allowed to stir at room temperature over night. Excess reagent was quenched by the addition of methanol (1 mL) and the mixture was concentrated under reduced pressure. The crude residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The extracts were washed with 1 M sodium hydroxide, saturated aqueous sodium thiosulfate and brine, dried over sodium sulfate, filtered, concentrated and purified by silica gel chromatography (3:1 methylene chloride/methanol) (77 mg, 94%).

Workup

  1. customExcess reagent was quenched by the addition of methanol (1 mL)
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe crude residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. washThe extracts were washed with 1 M sodium hydroxide, saturated aqueous sodium thiosulfate and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (3:1 methylene chloride/methanol) (77 mg, 94%)

Sources & evidence

ORD record
ord-73fd8fecce2d48ac93c09fc0a7960966
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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