Trimethylsilyldiazomethane → Methyl 1-(3-bromo-5-cyanophenyl)piperidine-4-carboxylate

HRID 40751

Reaction equation

HRID 40751 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=[O:17])[CH2:12][CH2:11]2)[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:20]>C1(C)C=CC=CC=1.CO>[Br:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:11][CH2:12][CH:13]([C:16]([O:18][CH3:20])=[O:17])[CH2:14][CH2:15]2)[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 595881891-(3-Bromo-5-cyanophenyl)piperidine-4-carboxylic acid

Product 1

HCID 59588037Methyl 1-(3-bromo-5-cyanophenyl)piperidine-4-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1-(3-bromo-5-cyanophenyl)piperidine-4-carboxylic acid (1.1 g, 3.6 mmol) in toluene (4 mL) and methanol (2 mL) was added TMSCHN2 (2 M in Et2O, 3.5 mL, 7.0 mmol) dropwise at room temperature. After 1 h, the reaction was quenched with acetic acid (˜0.1 mL), diluted with EtOAc and washed with saturated aqueous NaHCO3. The organic layer was separated, dried (MgSO4), and concentrated to give methyl 1-(3-bromo-5-cyanophenyl)piperidine-4-carboxylate in ˜100% yield.

Workup

  1. customthe reaction was quenched with acetic acid (˜0.1 mL)
  2. additiondiluted with EtOAc
  3. washwashed with saturated aqueous NaHCO3
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-852a98529a0f4ee78c517dafdbe85afc
Source dataset
uspto-grants-2013_09
Patent number
US08530480B2

Linked notes

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