Pentane → (S)-N-((2S,3S)-1,2-bis(tert-butyldimethylsilyloxy)-6-(trimethylsilyl)hex-5-yn-3-yl)-2-methylpropane-2-sulfinamide

HRID 1921961

反応式

HRID 1921961 の反応式
[CH3:1][Si:2]([CH3:7])([CH3:6])[C:3]#[C:4][CH3:5].CN(C)C(N(C)C)C.C([Li])(C)(C)C.CCCCC.[Si:26]([O:33][C@H:34]([CH2:43][O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])/[CH:35]=[N:36]/[S@:37]([C:39]([CH3:42])([CH3:41])[CH3:40])=[O:38])([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>C(OCC)C.C1COCC1>[Si:45]([O:44][CH2:43][C@@H:34]([O:33][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28])[C@@H:35]([NH:36][S@:37]([C:39]([CH3:40])([CH3:41])[CH3:42])=[O:38])[CH2:5][C:4]#[C:3][Si:2]([CH3:7])([CH3:6])[CH3:1])([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46]

参加物

8

反応物 5

HCID 8003PentaneHCID 803631-(Trimethylsilyl)prop-1-yneHCID 17803068N~1~,N~1~,N'~1~,N'~1~-Tetramethylethane-1,1-diamineHCID 44239381(NE,S)-N-[(2S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]propylidene]-2-methylpropane-2-sulfinamideHCID 178418306HCID 178418306、化合物

生成物 1

HCID 86627014(S)-N-((2S,3S)-1,2-bis(tert-butyldimethylsilyloxy)-6-(trimethylsilyl)hex-5-yn-3-yl)-2-methylpropane-2-sulfinamide

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Trimethyl(prop-1-ynyl)silane (4 mL, 28 mmol) and N,N,N′,N′-tetramethylethanediamine (5 mL, 36 mmol) were dissolved in dry diethyl ether (50 mL) and cooled to −78° C. Tert-butyllithium, 1.7 M solution in pentane (17 mL, 28 mmol) was added dropwise and the heterogenous solution was allowed to warm to 0° C. for 15 min to give a clear yellow solution, which was recooled to −78 C. Azeotropically (S,E)-N—((S)-2,3-bis(tert-butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide (3.0 g, 7 mmol) in dry THF (20 μL) was added dropwise and the solution was stirred for 1 h until the starting material was consumed. The reaction mixture as quenched with NH4Cl and extracted with EtOAc. The combined organics were washed with water, brine, dried over Na2SO4, filtered, and concentrated to afford a yellow oil as (S)—N-((2S,3S)-1,2-bis(tert-butyldimethylsilyloxy)-6-(trimethylsilyl)hex-5-yn-3-yl)-2-methylpropane-2-sulfinamide.

後処理

  1. temperatureto warm to 0° C. for 15 min
  2. customto give a clear yellow solution, which
  3. customwas consumed
  4. customThe reaction mixture as quenched with NH4Cl
  5. extractionextracted with EtOAc
  6. washThe combined organics were washed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-d0785bb3a6df4a7f9518a3ae0ef123f8
出典データセット
uspto-grants-2012_05
特許番号
US08173810B2

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