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Triethylamine → tert-butyl ((1S)-2-hydroxy-1-{3-[(trimethylsilyl)ethynyl]benzyl}ethyl)carbamate

HRID 339976
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인쇄 미리보기

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HRID 339976 반응식
[OH:1][CH2:2][C@@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](I)[CH:6]=1.C(N(CC)CC)C.[CH3:27][Si:28]([C:31]#[CH:32])([CH3:30])[CH3:29]>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[OH:1][CH2:2][C@@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:32]#[C:31][Si:28]([CH3:30])([CH3:29])[CH3:27])[CH:6]=1
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참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 86681468tert-Butyl [(1S)-2-hydroxy-1-(3-iodobenzyl)ethyl]carbamate

생성물 1

HCID 86681467tert-butyl ((1S)-2-hydroxy-1-{3-[(trimethylsilyl)ethynyl]benzyl}ethyl)carbamate수율 93%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

tert-Butyl [(1S)-2-hydroxy-1-(3-iodobenzyl)ethyl]carbamate (1.0 g, 2.6 mmol), copper(I) iodide (0.020 g, 0.11 mmol), bis(triphenylphosphine)palladium(II) chloride (0.074 g, 0.11 mmol), tetrahydrofuran (7 mL), and triethylamine (0.41 mL, 2.9 mmol) were combined. The reaction mixture was stirred under N2 for 5 min. (Trimethylsilyl)acetylene (1.1 mL, 8.0 mmol) was then added. The reaction mixture was stirred at 65° C. for 1 h, then evaporated under vacuum. The residue was purified by combi-flash chromatography to give 0.84 g (91% yield) of the desired product as light brown solid. LC-MS found: 248.0 (M−Boc+H)+.

후처리

  1. additionwas then added
  2. customevaporated under vacuum
  3. customThe residue was purified by combi-flash chromatography

출처 및 근거

ORD 기록
ord-cf6e89985bda4174937d4743d0083d46
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08895571B2

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