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

HRID 863267
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HRID 863267 반응식
[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]
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HCID 21225700DiisobutylaluminumhydrideHCID 22882589methyl 2(S)-tert-butoxycarbonylamino-4(S)-methyl-6-triisopropylsilyloxyhexanoate

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
-75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2ec12b3fe2784035b4ba6ad867af0864
출처 데이터셋
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05719141

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