Cyclobutanone → tert-butyl (2R)-2-[(4-benzylpiperazin-1-yl)carbonyl]-4-cyclobutylpiperazine-1-carboxylate

HRID 603194ノート

反応式

HRID 603194 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C@H:16]2[CH2:21][NH:20][CH2:19][CH2:18][N:17]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:38]1(=O)[CH2:41][CH2:40][CH2:39]1.S([O-])([O-])(=O)=O.[Mg+2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C@H:16]2[CH2:21][N:20]([CH:38]3[CH2:41][CH2:40][CH2:39]3)[CH2:19][CH2:18][N:17]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 14496CyclobutanoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57656790tert-Butyl (2R)-2-[(4-benzylpiperazin-1-yl)carbonyl]piperazine-1-carboxylate

生成物 1

HCID 57656643tert-butyl (2R)-2-[(4-benzylpiperazin-1-yl)carbonyl]-4-cyclobutylpiperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

tert-Butyl (2R)-2-[(4-benzylpiperazin-1-yl)carbonyl]piperazine-1-carboxylate (4.5 g) was dissolved in tetrahydrofuran (300 ml) and stirred at room temperature. N,N-Diisopropylethylamine (5.95 ml) was added followed by cyclobutanone (3.25 g) and magnesium sulphate (300 mg). After 45 minutes, sodium triacetoxyborohydride (9.78 g) was added and stirring continued overnight. Inorganic residues were removed by filtration and the filtrate concentrated in vacuo. The residue was purified by chromatography eluting with 0-10% methanol/dichloromethane. This gave tert-butyl (2R)-2-[(4-benzylpiperazin-1-yl)carbonyl]-4-cyclobutylpiperazine-1-carboxylate as a colourless gum (5.12 g).

後処理

  1. stirringstirring continued overnight
  2. customInorganic residues were removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified by chromatography
  5. washeluting with 0-10% methanol/dichloromethane

出典と根拠

ORDレコード
ord-3bce16e8f2734f478778ecfdc2855cc5
出典データセット
uspto-grants-2011_03
特許番号
US07906645B2

反応ノート

読み込み中…