Hydrogen Peroxide → HCID 21309361, compound

HRID 1075548Notes

Reaction equation

HRID 1075548 reaction equation
[C:1]([O:5][C@H:6]1[CH2:15][CH2:14][CH2:13][C@@H:12]2[C@:7]1([CH3:17])[CH2:8][CH2:9][CH2:10][C:11]2=[O:16])([CH3:4])([CH3:3])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[OH-].[Na+].OO>O1CCCC1.O>[C:1]([O:5][C@H:6]1[CH2:15][CH2:14][CH2:13][C@@H:12]2[C@:7]1([CH3:17])[CH2:8][CH2:9][CH2:10][C@@H:11]2[OH:16])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 21309365HCID 21309365, compound

Product 1

HCID 21309361HCID 21309361, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.12 g (8.9 mMol) of (4aS,5S,8aR)-5-tert-Butoxy4a-methyl-octahydro-naphtalen-1-one in 44.5 ml tetrahydrofuran was cooled to -78° C. and 9.8 ml (9.8 mMol) of a one molar solution of L-selectride in tetrahydrofuran was added dropwise under stirring and argon atmosphere. The reaction mixture was kept at this temperature for an additional hour, warmed to room temperature and kept overnight. The temperature was then lowered to -15° C. and 0.17 ml of H2O were added dropwise. This was followed by dropwise addition of 7.60 ml 3N NaOH and 6.36 ml of H2O2. The reaction temperature is kept between -10 to -15° C. The reaction mixture is then poured into water and extracted three times with ethylacetate. The combined organic extracts are washed with brine and evaporated in vacuo to dryness. The residue is chromatographed over 120 g of silicagel with hexane/ethylacetate 4/1 to yield 1.03 g (48%) of pure (1S,4aS,5S,8aR)-5-tert-Butoxy-4a-methyl-decahydronaphtalen-1-ol as an amorphous product.

Workup

  1. waitThe reaction mixture was kept at this temperature for an additional hour
  2. customwas then lowered to -15° C.
  3. customis kept between -10 to -15° C
  4. extractionextracted three times with ethylacetate
  5. washThe combined organic extracts are washed with brine
  6. customevaporated in vacuo to dryness
  7. customThe residue is chromatographed over 120 g of silicagel with hexane/ethylacetate 4/1

Sources & evidence

ORD record
ord-c6e1df6361f94667b9e136ac12a58975
Source dataset
uspto-grants-1999_05
Patent number
US05905074

Reaction notes

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