Hydrochloric Acid → HCID 67718682, compound

HRID 375444Notes

Reaction equation

HRID 375444 reaction equation
[ClH:1].[C:2]([O:5][CH:6]1[CH2:14][C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]2[CH:8]([CH2:9][N:10](C(OC=C)=O)[CH2:11]2)[C:7]1=[O:32])(=[O:4])[CH3:3]>O1CCOCC1>[ClH:1].[C:2]([O:5][CH:6]1[CH2:14][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]2[CH:8]([CH2:9][NH:10][CH2:11]2)[C:7]1=[O:32])(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67718820HCID 67718820, compound

Product 1

HCID 67718682HCID 67718682, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

394 cm3 of a 5.2N solution of hydrochloric acid in dioxane are added to a solution of 51.2 g of (3aRS,5RS,7aRS)-5-acetoxy-7,7-diphenyl-2-vinyloxycarbonylperhydroisoindolin-4-one in 118 cm3 of dioxane at room temperature. The reaction mixture is stirred at this temperature for 1 hour and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is recrystallized from 200 cm3 of boiling ethanol. 13.4 g of (3aRS,5RS,7aRS)-5-acetoxy-7,7-diphenylperhydroisoindol-4-one hydrochloride are obtained in the form of white crystals which melt at a temperature above 300° C.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  2. customThe residue is recrystallized from 200 cm3 of boiling ethanol

Sources & evidence

ORD record
ord-7131982f6196459283e5035672637802
Source dataset
uspto-grants-1996_01
Patent number
US05484804

Reaction notes

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