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Diisobutylaluminumhydride → 2(S)-tert-butoxycarbonylamino-4(S)-methyl-6-triisopropylsilyloxyhexanal

HRID 863267
ノート
印刷プレビュー

反応式

HRID 863267 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C@H:15]([CH3:29])[CH2:16][CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C@H:15]([CH3:29])[CH2:16][CH2:17][O:18][Si:19]([CH:20]([CH3:22])[CH3:21])([CH:23]([CH3:25])[CH3:24])[CH:26]([CH3:27])[CH3:28])[CH:10]=[O:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]
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

4

反応物 2

HCID 21225700DiisobutylaluminumhydrideHCID 22882589methyl 2(S)-tert-butoxycarbonylamino-4(S)-methyl-6-triisopropylsilyloxyhexanoate

生成物 1

HCID 228823932(S)-tert-butoxycarbonylamino-4(S)-methyl-6-triisopropylsilyloxyhexanal

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
-75 °C

実験手順

A solution of 3.35 g methyl 2(S)-tert-butoxycarbonylamino-4(S)-methyl-6-triisopropylsilyloxyhexanoate in 44 ml of toluene is cooled to -75° C. under argon, and 12.9 ml of a 20% solution of diisobutylaluminium hydride in toluene are then added dropwise in the course of 30 min. The mixture is stirred at -75° C. for a further 45 min. The reaction is then quenched by rapid addition of 2.8 ml of methanol and the mixture is poured onto 50 ml of a half-saturated aqueous potassium sodium tartrate solution. The mixture is extracted with diethyl ether and the combined organic phases are dried over sodium sulfate and concentrated. The title compound (Rf (E)=0.34) is further reacted directly as the crude product.

後処理

  1. customThe reaction is then quenched by rapid addition of 2.8 ml of methanol
  2. additionthe mixture is poured onto 50 ml of a half-saturated aqueous potassium sodium tartrate solution
  3. extractionThe mixture is extracted with diethyl ether
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe title compound (Rf (E)=0.34) is further reacted directly as the crude product

出典と根拠

ORDレコード
ord-2ec12b3fe2784035b4ba6ad867af0864
出典データセット
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05719141

反応ノート

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