Trimethylsilyldiazomethane → Methyl 3-amino-3-cyclobutylpropanoate

HRID 2171853ノート

反応式

HRID 2171853 の反応式
[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]

参加物

7

反応物 2

HCID 167693TrimethylsilyldiazomethaneHCID 247302513-Amino-3-cyclobutylpropanoic acid2 回

生成物 1

HCID 73425272Methyl 3-amino-3-cyclobutylpropanoate収率 95%

試薬・触媒・溶媒 4

HCID 241Benzene溶媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-6fbe25dadfa4454a879c104628e750fb
出典データセット
uspto-grants-2015_06
特許番号
US09051319B2

反応ノート

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