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

HRID 1473864

반응식

HRID 1473864 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-07c2731fe3b149f6bccda5e10169d711
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018205B2

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