Tetrabutylammonium Fluoride Trihydrate → (1S,4aS,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl]-4a-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol

HRID 581607Notes

Reaction equation

HRID 581607 reaction equation
[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][CH:32]=[C: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:33]1[C@:34]2([CH3:38])[C@@H:29]([CH2:30][CH2:31][CH:32]=1)[C@@H:28]([OH:27])[CH2:37][CH2:36][CH2:35]2)[CH3:47]

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 57153816(R)-6-[(4aR,5S,8aS)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-2-methyl-hept-3-yn-2-ol

Product 1

HCID 86754179(1S,4aS,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl]-4a-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-olYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.43 g (17.2 mmol) of nBu4NF.3H2O in 10 ml of THF was carefully dried by stirring during 2 h at RT over 7.5 g of 3 Å molecular sieve. This solution was then added to 866 mg (2.14 mmol) of (R)-6-[(4aR,5S,8aS)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-2-methyl-hept-3-yn-2-ol and the mixture kept for 24 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=7/3) afforded 590 mg of the title compound as colorless oil.

Workup

  1. waitthe mixture kept for 24 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

Sources & evidence

ORD record
ord-67018e4ba92649e19a6b5a0809f3945d
Source dataset
uspto-grants-1999_07
Patent number
US05919986

Reaction notes

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