Trimethylsilyldiazomethane → HCID 178421608, compound

HRID 353115Notes

Reaction equation

HRID 353115 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])[CH2:22][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)[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 22707903HCID 22707903, compoundHCID 178418339Butyllithium

Product 1

HCID 178421608HCID 178421608, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (trimethylsilyl)diazomethane (2.0 M in hexane, 0.55 mL, 1.10 mmol) in tetrahydrofuran (5 mL) at 0° C. under an atmosphere of nitrogen was added n-butyllithium (1.6 M in hexane, 0.69 mL, 1.10 mmol) dropwise. After 1 h, a solution of 1-benzyl-4-(3-cyanophenyl)-4-methylpiperidine (Preparation 9, 300 mg, 1.03 mmol) in tetrahydrofuran (10 mL) was added such that the internal temperature remained at 0° C. After 4.5 h, the reaction was quenched with saturated sodium hydrogencarbonate (25 mL) and the mixture was extracted with diethyl ether (3×25 mL). The extracts were washed with water (10 mL) and brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as a foam (360 mg, 86%).

Workup

  1. customremained at 0° C
  2. waitAfter 4.5 h
  3. customthe reaction was quenched with saturated sodium hydrogencarbonate (25 mL)
  4. extractionthe mixture was extracted with diethyl ether (3×25 mL)
  5. washThe extracts were washed with water (10 mL) and brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fab65eac92c47ae85e661af13d4da22
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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