Hydrochloric Acid → HCID 20145926, compound

HRID 2295508Notes

Reaction equation

HRID 2295508 reaction equation
B#B.[OH-:3].[Na+].OO.Cl.[O:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH3:9][OH:8].[CH3:10][CH2:9][O:8][CH2:12][CH3:11].[C:12]([O-:8])(=[O:3])[CH3:11]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 6328200Diboron

Product 1

HCID 20145926HCID 20145926, compound

Procedure

24 ml of a 1 M diborane solution in tetrahydrofuran are added drop-wise over 2 hours at a temperature of -10° C. to a solution of 2.02 g (6 mMol) of 5-allyloxy-2'-methoxy-2,9,9-trimethyl-6,7-benzomorphan hydrochloride (c.f. example 8f) in 25 ml of tetrahydrofuran. After stirring for 4 hours at room-temperature 16 ml of a 1 N sodium hydroxide solution and 2 ml 30% hydrogen peroxide are carefully added drop-wise. After reaction for 1 hour at room-temperature, 30 ml 1 N hydrochloric acid are added and the mixture is boiled for a further 1 hour under reflux. The tetrahydrofuran is distilled off under reduced pressure, the acid aqueous phase rendered alkali with 25% ammonia and extracted 3 times with 25 ml chloroform. The combined chloroformic phases are dried over magnesium sulphate and concentrated under reduced pressure. After conversion of the residue into the hydrochloric and crystallition from methanol/ether acetate 1.15 g of the title compound are obtained, m.p.: 187°-193° C.

Workup

  1. additionare added
  2. temperatureunder reflux
  3. distillationThe tetrahydrofuran is distilled off under reduced pressure
  4. extractionextracted 3 times with 25 ml chloroform
  5. dry with materialThe combined chloroformic phases are dried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9185ba86068408995e758f3e200641a
Source dataset
uspto-grants-1984_01
Patent number
US04425353

Reaction notes

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