Hydrochloric Acid → HCID 67916057, compound

HRID 1029888Notes

Reaction equation

HRID 1029888 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([N:19]1[CH2:27][CH:26]2[CH:21]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:23][CH2:24][C:25]2=[O:28])[CH2:20]1)=[O:18])=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17]([N:19]1[CH2:27][CH:26]2[CH:21]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:23][CH2:24][C:25]2=[O:28])[CH2:20]1)=[O:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67915951HCID 67915951, compound

Product 1

HCID 67916057HCID 67916057, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(3aRS,7aRS)-2-[(2-(tert-butoxycarbonylaminomethyl)phenyl)acetyl]-7,7-diphenyl-4-perhydroisoindolone (1 g) is treated with a 5.7N solution (10 cc) of hydrochloric acid in dry dioxane at 20° C. for 16 hours. The reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is solidified by scratching with isopropyl ether and reprecipitated by cooling a solution in boiling acetonitrile (20 cc). The solid is drained, washed with isopropyl ether and dried. The solid is dissolved in water, the solution is filtered, rendered alkaline to pH 10 by the action of a decinormal sodium hydroxide solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and filtered and the filtrate is treated with a 3N solution (1 cc) of hydrochloric acid in dioxane. The precipitate is drained, washed with isopropyl ether and dried. (3aRS,7aRS)-2-[(2-aminomethylphenyl)acetyl]-7,7-diphenyl-4-perhydroisoindolone (0.5 g) is obtained in the form of a cream-white solid.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customreprecipitated
  3. temperatureby cooling a solution
  4. washwashed with isopropyl ether
  5. customdried
  6. dissolutionThe solid is dissolved in water
  7. filtrationthe solution is filtered
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic phase is dried over magnesium sulphate
  10. filtrationfiltered
  11. additionthe filtrate is treated with a 3N solution (1 cc) of hydrochloric acid in dioxane
  12. washwashed with isopropyl ether
  13. customdried

Sources & evidence

ORD record
ord-7a248205f7634806a0ccb87c6cd97b15
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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