Hydrochloric Acid → (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride

HRID 2211400Notes

Reaction equation

HRID 2211400 reaction equation
[ClH:1].[C:2]1([C:8]2([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@@H:16]3[C@@H:12]([CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15]3)[C@@:11]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])([OH:24])[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1>[ClH:1].[C:33]1([C:8]2([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:16]3[C@@H:12]([CH2:13][NH:14][CH2:15]3)[C@@:11]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])([OH:24])[CH2:10][CH2:9]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22857048HCID 22857048, compound

Product 1

HCID 70218598(3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

100 cm3 of a 5.2N solution of hydrogen chloride in dioxane are added to a solution of 7.63 g of (3aS, 4S, 7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-tert-butoxycarbonyl-perhydroisoindol-4-ol in 66 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 washed with acetonitrile, filtered off and then dried. 4.88 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2 -methoxyphenyl)-perhydroisoindol-4-ol hydrochloride are obtained in the form of white crystals which melt at 271° C. (Maquenne block).

Workup

  1. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  2. washThe residue is washed with acetonitrile
  3. filtrationfiltered off
  4. customdried

Sources & evidence

ORD record
ord-d45e8f2122c2421aa80d44f44529b4fd
Source dataset
uspto-grants-1995_10
Patent number
US05463077

Reaction notes

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