Trimethylsilyldiazomethane → Methyl 3-amino-3-cyclobutylpropanoate

HRID 1055056노트

반응식

HRID 1055056 반응식
[NH2:1][CH:2]([CH:7]1[CH2:10][CH2:9][CH2:8]1)[CH2:3][C:4]([OH:6])=[O:5].[N+](=[CH:13][Si](C)(C)C)=[N-]>CO.C1C=CC=CC=1.CCOC(C)=O.[Cl-].[Na+].O>[NH2:1][CH:2]([CH:7]1[CH2:10][CH2:9][CH2:8]1)[CH2:3][C:4]([O:6][CH3:13])=[O:5]

참가 물질

7

반응물 2

HCID 167693TrimethylsilyldiazomethaneHCID 247302513-Amino-3-cyclobutylpropanoic acid2회

생성물 1

HCID 73425272Methyl 3-amino-3-cyclobutylpropanoate수율 95%

시약·촉매·용매 4

HCID 241Benzene용매HCID 887Methanol용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of racemic 3-amino-3-cyclobutyl-propanoic acid, 48a, (0.34 g, 2.38 mmol) in MeOH (10.2 mL) and benzene (10.2 mL) was added diazomethyltrimethyl-silane (3.56 mL of 2 M solution, 7.13 mmol) and the reaction mixture was allowed to stir at room temperature under a nitrogen atmosphere overnight. The mixture was diluted with EtOAc and brine. The layers were separated and the organic phase was dried (MgSO4), filtered and concentrated in vacuo to afford 354 mg (95%) of crude product that was used without further purification: 1H NMR (400 MHz, CDCl3) δ 3.71-3.66 (m, 3H), 3.18-2.98 (m, 1H), 2.46-2.32 (m, 2H), 2.27-1.63 (m, 10H).

후처리

  1. customThe layers were separated
  2. dry with materialthe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4c506a6a47124e3882d7ed7665ee4e89
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394302B2

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