Trimethylsilyldiazomethane → HCID 178444685, compound

HRID 353105Notes

Reaction equation

HRID 353105 reaction equation
[CH3:1][Si:2]([CH:5]=[N+:6]=[N-:7])([CH3:4])[CH3:3].C([Li])CCC.[C:13]([C:15]1[CH:16]=[C:17]([C:21]2([CH3:34])[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:23][CH:22]2[CH3:33])[CH:18]=[CH:19][CH:20]=1)#[N:14]>O1CCCC1>[CH2:27]([N:24]1[CH2:25][CH2:26][C:21]([CH3:34])([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:13]3[N:14]=[N:7][NH:6][C:5]=3[Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:16]=2)[CH:22]([CH3:33])[CH2:23]1)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 22645388HCID 22645388, compoundHCID 178418339Butyllithium

Product 1

HCID 178444685HCID 178444685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (trimethylsilyl)diazomethane (2.0 M in hexane, 400 μL, 0.80 mmol) in tetrahydrofuran (10 mL) at 0° C. under an atmosphere of nitrogen was added n-butyllithium (2.5 M in diethyl ether, 320 μL, 0.80 mmol) dropwise. After 20 min, a solution of 4-(3-cyanophenyl)-1-hexyl-3,4-dimethylpiperidine (Preparation 6, 200 mg, 0.67 mmol) in tetrahydrofuran (5 mL) was added such that the internal temperature remained at 0° C. After stirring overnight, the reaction was quenched with saturated aqueous sodium hydrogencarbonate (25 mL) and the mixture was extracted with diethyl ether (3×25 mL). The extracts were washed with water and brine (10 mL each), dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a white foam which was used without further purification (266 mg, 96%).

Workup

  1. customremained at 0° C
  2. customthe reaction was quenched with saturated aqueous sodium hydrogencarbonate (25 mL)
  3. extractionthe mixture was extracted with diethyl ether (3×25 mL)
  4. washThe extracts were washed with water and brine (10 mL each)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c6a45dcd1ab417fa128cab5dd310be6
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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