N-Hydroxyphthalimide → Benzyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate

HRID 710951ノート

反応式

HRID 710951 の反応式
[CH2:1]([O:8][C:9](=[O:14])[NH:10][CH2:11][CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45].C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([O:8][C:9](=[O:14])[NH:10][CH2:11][CH2:12][O:13][N:35]1[C:39](=[O:40])[C:38]2[C:37](=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:36]1=[O:45])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 280458benzyl N-(2-hydroxyethyl)carbamateHCID 66777355Diethylazodicarboxylate toluene

生成物 1

HCID 13983475Benzyl (2-((1,3-dioxoisoindolin-2-yl)oxy)ethyl)carbamate収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Benzyl(2-hydroxyethyl)carbamate (5.857 g, 30.0 mmol) was stirred under an argon atmosphere at room temperature with dehydrated tetrahydrofuran (150 mL). Then, triphenylphosphine (7.90 g) and N-hydroxyphthalimide (Pht-OH, 4.89 g) were added. After the reaction mixture was under ice cooling, 2.2M diethyl azodicarboxylate toluene solution (13.7 mL) was added dropwise gradually, followed by stirring overnight at room temperature. After completion of the reaction, the residue resulting from distilling off the solvent under reduced pressure was subjected to silica gel column chromatography (hexane/ethyl acetate=1/1) to afford 9.36 g of the title compound (yield 92%).

後処理

  1. customAfter completion of the reaction
  2. customthe residue resulting
  3. distillationfrom distilling off the solvent under reduced pressure

出典と根拠

ORDレコード
ord-a5913e2debed412cbcd55455a115d899
出典データセット
uspto-grants-2015_11
特許番号
US09181250B2

反応ノート

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