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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
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Toluene → HCID 117925141、化合物

HRID 705715
ノート
印刷プレビュー

反応式

HRID 705715 の反応式
[C:1]([O:5][C:6]([N:8]1[C@H:14]([CH2:15]O)[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[C@H:14]([CH2:15][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[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

8

反応物 5

HCID 1140TolueneHCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 89872603tert-Butyl (1R,3S,6S)-3-(hydroxymethyl)-2-azabicyclo[4.1.0]heptane-2-carboxylate

生成物 1

HCID 117925141HCID 117925141、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A suspension of D7 (10 g, 44 mmol), phtalimide (10.29 g, 70 mmol) and triphenylphosphine (18.34 g, 70 mmol) in THF (150 mL) was cooled at 0° C., then a 40% solution of DEAD in toluene (31.94 mL, 70 mmol) was added. The mixture was stirred at room temperature for 3 hours, then water was added and the mixture was concentrated under vacuum; the residue was dissolved in DCM, washed with water and organics were evaporated. Cyclohexane (300 mL) and DCM (10 mL) were added, the precipitate was discarded and the filtrate was concentrated. The crude mixture was purified by silica gel column chromatography (cyclohexane/ethyl acetate=95:5 to 70/30) to give the title compound as a white solid. Yield (11 g, 71%).

後処理

  1. concentrationthe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water
  4. customorganics were evaporated
  5. additionCyclohexane (300 mL) and DCM (10 mL) were added
  6. concentrationthe filtrate was concentrated
  7. customThe crude mixture was purified by silica gel column chromatography (cyclohexane/ethyl acetate=95:5 to 70/30)

出典と根拠

ORDレコード
ord-27cb8e22c66545bcac440d3da6d74273
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09174977B2

反応ノート

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