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Phthalimide → (S)-2-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)isoindoline-1,3-dione

HRID 2279451
ノート
印刷プレビュー

反応式

HRID 2279451 の反応式
[Si:1]([O:8][CH2:9][C@@H:10]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([F:19])[CH:13]=1)O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20]1(=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:29])[NH:21]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1.C1COCC1>[Si:1]([O:8][CH2:9][C@@H:10]([N:21]1[C:22](=[O:29])[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]1=[O:30])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([F:19])[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86696647(R)-2-((tert-butyldimethylsilyl)oxy)-1-(4-chloro-3-fluorophenyl)ethanol

生成物 1

HCID 68294575(S)-2-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)isoindoline-1,3-dione収率 74.7%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 64 (13.50 g, 44.28 mmol) and THF (150 mL) cooled to 0° C. was added isoindoline-1,3-dione (7.167 g, 48.71 mmol) and PPh3 (17.42 g, 66.42 mmol) followed by the dropwise addition of a 40% solution DEAD (26.15 mL, 66.42 mmol) in toluene. The reaction was warmed to RT and stirred for 20 h. The reaction was concentrated and dissolved in Et2O (might require sonication). The solids were filtered and the filtrate was concentrated. The crude residue was purified by SiO2 chromatography (Biotage 65) eluting with 10% EtOAc/hexane to afford 14.35 g of (74.67%) (S)-2-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)isoindoline-1,3-dione (66).

後処理

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in Et2O (might require sonication)
  3. filtrationThe solids were filtered
  4. concentrationthe filtrate was concentrated
  5. customThe crude residue was purified by SiO2 chromatography (Biotage 65)
  6. washeluting with 10% EtOAc/hexane

出典と根拠

ORDレコード
ord-712bda607fa74f87bec6d037616bfd63
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133187B2

反応ノート

読み込み中…

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