Triethylsilane → HCID 22615744, compound

HRID 366499Notes

Reaction equation

HRID 366499 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].[CH2:12]([O:19][C:20]([N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C([SiH](CC)CC)C>C(#N)C.C(OCC)(=O)C>[CH2:12]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=3)[NH:8][CH:7]=2)[CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 12052TriethylsilaneHCID 27513Indole-5-carbonitrileHCID 65367Trimethylsilyl triflateHCID 643496Benzyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 22615744HCID 22615744, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-cyanoindole (10.00 g, 70.34 mmol) in acetonitrile (120 ml) was added to a solution of 1-benzyloxycarbonyl-4-piperidone (8.20 g, 35.17 mmol) and trimethylsilyl trifluoromethanesulfonate (6.80 ml, 35.17 mmol) in acetonitrile (230 ml) via addition funnel at 0° C. over 1.5 h. Triethylsilane (4.2 ml, 26.28 mmol) was added at 0° C. and reaction mixture was allowed to gradually warm to RT over 2 h. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate, brine, dried over MgSO4, and concentrated in vacuo. The residue was diluted with acetonitrile (300 ml) and hexanes (200 ml) and stirred for 20 min. The organics were removed in vacuo and the residue was chromatographed (SiO2, 20-40% ethyl acetate/hexanes) to give 1-benzyloxycarbonyl-4-(5-cyanoindol-3-yl)piperidine as a white crystalline solid (59%).

Workup

  1. customreaction mixture
  2. washwashed with saturated sodium bicarbonate, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with acetonitrile (300 ml) and hexanes (200 ml)
  6. customThe organics were removed in vacuo
  7. customthe residue was chromatographed (SiO2, 20-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7160f7cfcfc241bb85a4c654d904fdb0
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Reaction notes

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