Trimethylamine oxide → HCID 20230969, compound

HRID 2290499Notes

Reaction equation

HRID 2290499 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:11][CH2:10][CH:9]([CH3:12])[C:8]2[CH2:7]C(C)=CC[C:3]1=2.C[N+]([O-:19])(C)C.[C:20]([OH:24])([CH3:23])([CH3:22])[CH3:21]>O.CCOCC.[Os](=O)(=O)(=O)=O>[CH3:1][C:2]1([CH3:14])[CH2:11][CH2:10][CH:9]([CH3:12])[C:8]2[CH2:7][CH:22]([OH:19])[C:20]([CH3:23])([OH:24])[CH2:21][C:3]1=2

Participants

7

Reactant 3

HCID 1145Trimethylamine oxideHCID 6386tert-Butanol2×HCID 20230962HCID 20230962, compound

Product 1

HCID 20230969HCID 20230969, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

24 g of crude 2,2,5,8-tetramethyl-bicyclo[4.4.0]deca-1(6),8-diene (43%) in 120 ml of tert.butanol are treated with a solution of 10.5 g of trimethylamine N-oxide in 43 ml of water in a three-necked sulphonation flask equipped with a stirrer, a reflux condenser, a thermometer and an argon flow with a bubble counter. 50 ml of a 0.05% solution of osmium tetroxide in tert.butanol are added thereto. The resulting emulsion is held at reflux temperature for 96 hours with good stirring. The cooled solution is diluted with ether and washed with a saturated sodium chloride solution, with 2N hydrochloric acid and with ice-water. The aqueous phases are extracted twice with ether. After drying the combined organic phases over magnesium sulphate and concentration on a rotary evaporator, 24 g of crude product was obtained. By recrystallization from hexane there are obtained 6 g of 2,2,5,9-tetramethyl-bicyclo[4.4.0]dec-1(6)-ene-8,9-diol of melting point 121°-123° C.

Workup

  1. customequipped with a stirrer, a reflux condenser
  2. temperatureat reflux temperature for 96 hours with good stirring
  3. washwashed with a saturated sodium chloride solution, with 2N hydrochloric acid and with ice-water
  4. extractionThe aqueous phases are extracted twice with ether
  5. customAfter drying the combined organic phases
  6. concentrationover magnesium sulphate and concentration
  7. customon a rotary evaporator
  8. custom24 g of crude product was obtained
  9. customBy recrystallization from hexane

Sources & evidence

ORD record
ord-d826b8691e774cc7a6ab35c2983c01da
Source dataset
uspto-grants-1986_10
Patent number
US04617146

Reaction notes

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