Hydrogen Peroxide → HCID 18396005, compound

HRID 1858998Notes

Reaction equation

HRID 1858998 reaction equation
[C:1]([O:5][C@H:6]1[CH2:15][CH2:14][CH2:13][C:12]2[C@:7]1([CH3:17])[CH2:8][CH2:9][C:10](=[O:16])[CH:11]=2)([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:12]2[C@:7]1([CH3:17])[CH2:8][CH2:9][C@H:10]([OH:16])[CH:11]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 6543862rel-(4aR,5R)-5-(1,1-Dimethylethoxy)-4,4a,5,6,7,8-hexahydro-4a-methyl-2(3H)-naphthalenone

Product 1

HCID 18396005HCID 18396005, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 30.1 g (0.13 mole) (4aS,5S)-5-tert-butoxy-4a-methyl-4,4a, 5,6,7,8-hexahydro-2(3H)-naphtalenone in 600 ml tetrahydrofurane was cooled under stirring and Argon atmosphere to -78° C. After dropwise addition of 140 ml (0.14 mole) of L-selectride (1 molar in tetrahydrofurane),the reaction mixture was kept at -78° C. for an additional hour, then warmed to room temperature and kept at this temperature for 4.5 hours. After cooling to -15° C., 12 ml of H2O, 90 ml of 4N NaOH and 100 ml of H2O2 (30%) were added sequentially and dropwise by keeping the temperature between -10° C. to -15° C. After completed addition the reaction mixture was warmed to room temperature, poured onto water and extracted three times with ethylacetate. The combined organic layers were dried with sodium sulfate and evaporated after filtration to yield 30 g of crude (2S,4aS,5S)-5-tert-butoxy-4a-methyl-2,3,4,4a,5,6,7,8-octahydro-naphtalen-2-ol as an amorphous product shown by thin layer chromatography and NMR to be sufficiently pure for further transformations.

Workup

  1. customto -78° C
  2. waitwas kept at -78° C. for an additional hour
  3. temperatureAfter cooling to -15° C.
  4. custombetween -10° C. to -15° C
  5. additionaddition the reaction mixture
  6. temperaturewas warmed to room temperature
  7. additionpoured onto water
  8. extractionextracted three times with ethylacetate
  9. dry with materialThe combined organic layers were dried with sodium sulfate
  10. customevaporated
  11. filtrationafter filtration

Sources & evidence

ORD record
ord-91c866a7383141709b3338214efc6de2
Source dataset
uspto-grants-2000_11
Patent number
US06153605

Reaction notes

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