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Phthalimide → 2-[4-(1-Tertbutoxycarbonylpiperidin-4-yl)-butyl]-isoindol-1,3-dione

HRID 1294463
ノート
印刷プレビュー

反応式

HRID 1294463 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:38]1(=[O:48])[NH:42][C:41](=[O:43])[C:40]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:39]12.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:42]2[C:38](=[O:48])[C:39]3[C:40](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:41]2=[O:43])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2784670tert-Butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate

生成物 1

HCID 184257562-[4-(1-Tertbutoxycarbonylpiperidin-4-yl)-butyl]-isoindol-1,3-dione

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
15 °C

実験手順

136 g (<528 mmol) 4-[1-tert-butoxycarbonylpiperidin-4-yl)-butan-1-ol (crude product), 135.3 g (516 mmol) Triphenylphosphine and 75.9 g (516 mmol) phthalimide are suspended in 1800 ml THF and 89.9 g (516 mmol) azodicarboxylic acid diethyl ester are added dropwise within three hours under protective atmosphere and light cooling (to ca. 15° C.). The mixture is left to stand at RT overnight without further cooling. Subsequently, the solvent is removed under vacuum and the oily residue is dissolved in 500 ml acetic acid ethyl ester and held at 0° C. overnight. The sedimented precipitate is filtered and discarded. The solution is concentrated under vacuum and the oily residue is chromatographically purified over silica gel with CHCl3 and crystallized from 200 ml isopropanol after drawing off the solvent. Colorless crystals remain with a MP of 100–102° C.; yield: 108.5 g (57%).

後処理

  1. waitThe mixture is left
  2. customSubsequently, the solvent is removed under vacuum
  3. dissolutionthe oily residue is dissolved in 500 ml acetic acid ethyl ester
  4. waitheld at 0° C. overnight
  5. filtrationThe sedimented precipitate is filtered
  6. concentrationThe solution is concentrated under vacuum
  7. customthe oily residue is chromatographically purified over silica gel with CHCl3
  8. customcrystallized from 200 ml isopropanol

出典と根拠

ORDレコード
ord-66d01216535f4392b9239d22be161e03
出典データセット
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07241745B2

反応ノート

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