Trimethylsilyldiazomethane → HCID 178430275, compound

HRID 353103Notes

Reaction equation

HRID 353103 reaction equation
[CH3:1][Si:2]([CH:5]=[N+:6]=[N-:7])([CH3:4])[CH3:3].C([Li])CCC.[CH2:13]([N:20]1[CH2:25][CH2:24][C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]#[N:34])[CH:28]=2)([CH3:26])[CH:22]([CH3:35])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[CH2:13]([N:20]1[CH2:25][CH2:24][C:23]([CH3:26])([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]3[N:34]=[N:7][NH:6][C:5]=3[Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:28]=2)[CH:22]([CH3:35])[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 11358623HCID 11358623, compoundHCID 178418339Butyllithium

Product 1

HCID 178430275HCID 178430275, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (trimethylsilyl)diazomethane (2.0 M in hexane, 9.86 mL, 19.7 mmol) in tetrahydrofuran (40 mL) at 0° C. under an atmosphere of nitrogen was added n-butyllithium (2.5 M in hexane, 7.9 mL, 19.7 mmol) dropwise. After 30 min, a solution of 1-benzyl-4-(3-cyanophenyl)-3,4-dimethylpiperidine (Preparation 3, 5.0 g, 16.4 mmol) in tetrahydrofuran (40 mL) was added such that the internal temperature remained at 0° C. After stirring overnight, the reaction was quenched with saturated aqueous sodium hydrogencarbonate (100 mL) and the mixture was extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a pale brown foam (6.53 g, 79%).

Workup

  1. customremained at 0° C
  2. customthe reaction was quenched with saturated aqueous sodium hydrogencarbonate (100 mL)
  3. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64c2bc750df648a99ad280a27f93bfc3
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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