Hydrofluoric Acid → HCID 20638396, compound

HRID 1858995Notes

Reaction equation

HRID 1858995 reaction equation
C([Si](C)(C)[O:6][C@H:7]1[CH2:15][CH2:14][CH2:13][C@@:12]2([CH3:16])[C@H:8]1[CH2:9][CH2:10][C@@H:11]2[C@H:17]([CH3:20])[C:18]#[CH:19])(C)(C)C.F>C1COCC1.[Cl-].[Na+].O>[CH3:16][C@@:12]12[C@@H:11]([C@H:17]([CH3:20])[C:18]#[CH:19])[CH2:10][CH2:9][C@H:8]1[C@@H:7]([OH:6])[CH2:15][CH2:14][CH2:13]2

Participants

5

Reactant 2

HCID 14917Hydrofluoric AcidHCID 20638391HCID 20638391, compound

Product 1

HCID 20638396HCID 20638396, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Typically, the compound of formula IX, (1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-1-[(S)-1-methyl-propynyl]-octahydro-indene (900 mg; 2.81 mmol) was dissolved in THF (35 ml). Hydrofluoric acid (40% aqueous solution; 18 ml) was added and the reaction mixture was stirred at room temperature for three hours. The reaction mixture was then poured on chilled brine, extracted twice with ethyl acetate, washed twice with brine, dried over anhydrous sodium sulfate and the solvent was removed. After flash-chromatography (eluent: hexanes/ethyl-acetate 82/18) the compound [1R,3aR,4S,7aR]-7a-Methyl-1-[(S)-1-methyl-prop-2-ynyl]-octahydro-inden-4-ol (497 mg; yield: 86%) was obtained as a yellow oil.

Workup

  1. additionThe reaction mixture was then poured
  2. extractionextracted twice with ethyl acetate
  3. washwashed twice with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-1cf49157c6a94a3ba9e804603079fe4f
Source dataset
uspto-grants-2000_11
Patent number
US06153605

Reaction notes

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