Water → (1S,4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-decahydro-naphtalen-1-ol

HRID 1075556Notes

Reaction equation

HRID 1075556 reaction equation
C([Si](C)(C)[O:6][C@H:7]1[CH2:16][CH2:15][CH2:14][C@@:13]2([CH3:17])[C@H:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]2[C@H:18]([CH3:26])[CH2:19][CH2:20][CH2:21][C:22]([CH3:25])([OH:24])[CH3:23])(C)(C)C.C(#N)C.O>O1CCCC1>[OH:24][C:22]([CH3:23])([CH3:25])[CH2:21][CH2:20][CH2:19][C@H:18]([C@H:12]1[CH2:11][CH2:10][CH2:9][C@@H:8]2[C@:13]1([CH3:17])[CH2:14][CH2:15][CH2:16][C@@H:7]2[OH:6])[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 6342AcetonitrileHCID 21309367(R)-6-[(1R,4aR,5S,8aR)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-decahydronaphtalen-1-yl]-2-methyl-heptan-2-ol

Product 1

HCID 21309359(1S,4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-decahydro-naphtalen-1-olYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 267 mg (0.65 mMol) of (R)-6-[(1R,4aR,5S,8aR)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-decahydronaphtalen-1-yl]-2-methyl-heptan-2-ol in 2.5 ml of tetrahydrofuran are added 7.5 ml of acetonitrile and 2.5 ml of an aqueous HF solution (40%). The reaction mixture is kept for 72 hours, poured unto water and extracted three times with diethylether, the combined organic extracts are washed with a saturated aqueous NaHCO3 solution, with water, dried over Na2SO4, filtered and evaporated in vacuo. The residue is chromatographed over 40 g of silicagel with toluene/diethylether 4/1 to yield 107 mg (56%) of crystalline pure (1S,4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl -decahydro-naphtalen-1-ol. The material crystallized with diisopropylether has m.p.: 85.1-86.9°.

Workup

  1. extractionextracted three times with diethylether
  2. washthe combined organic extracts are washed with a saturated aqueous NaHCO3 solution, with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue is chromatographed over 40 g of silicagel with toluene/diethylether 4/1

Sources & evidence

ORD record
ord-29f881db444245e6b7c3b6282e01a2e0
Source dataset
uspto-grants-1999_05
Patent number
US05905074

Reaction notes

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