Tetrabutylammonium Fluoride Trihydrate → (1S,4aR,5R,8aR)-5-((R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-decahydro-naphthalen-1-ol

HRID 581612ノート

反応式

HRID 581612 の反応式
[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O.O.O.C([Si](C)(C)[O:27][C@H:28]1[CH2:37][CH2:36][CH2:35][C@@:34]2([CH3:38])[C@H:29]1[CH2:30][CH2:31][CH2:32][C@@H:33]2[C@H:39]([CH3:47])[CH2:40][C:41]#[C:42][C:43]([CH3:46])([OH:45])[CH3:44])(C)(C)C>C1COCC1>[OH:45][C:43]([CH3:44])([CH3:46])[C:42]#[C:41][CH2:40][C@H:39]([C@H:33]1[CH2:32][CH2:31][CH2:30][C@@H:29]2[C@:34]1([CH3:38])[CH2:35][CH2:36][CH2:37][C@@H:28]2[OH:27])[CH3:47]

参加物

4

反応物 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 57089693(R)-6-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-2-methyl-hept-3-yn-2-ol

生成物 1

HCID 57216772(1S,4aR,5R,8aR)-5-((R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-decahydro-naphthalen-1-ol収率 87.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

12.0 g (38.0 mmol) of nBu4NF.3H2O in 40 ml of THF was carefully dried by stirring during 2 h at RT over 15 g of 3 Å molecular sieve. This solution was then added to 1.93 g (4.748 mmol) of (R)-6-[(1R,4aR,5S,8aR)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-2-methyl-hept-3-yn-2-ol and the mixture kept for 40 h at 55°. The reaction mixture was then poured onto crushed ice, extracted twice with ether, washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) afforded 1.22 g of the title compound as white crystals of mp. 134-135°.

後処理

  1. waitthe mixture kept for 40 h at 55°
  2. additionThe reaction mixture was then poured
  3. customonto crushed ice
  4. extractionextracted twice with ether
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness

出典と根拠

ORDレコード
ord-318a3761522c41a69f2029809f3024e3
出典データセット
uspto-grants-1999_07
特許番号
US05919986

反応ノート

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