Hydrochloric Acid → (3aR,7S,7aR)-7-chloro-4,4-diphenyl-perhydroisoindole hydrochloride

HRID 2400002Notes

Reaction equation

HRID 2400002 reaction equation
Cl.C(OC([N:9]1[CH2:17][C@@H:16]2[C@@H:11]([C@@H:12]([Cl:30])[CH2:13][CH2:14][C:15]2([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10]1)=O)(C)(C)C>O1CCOCC1>[ClH:30].[Cl:30][C@@H:12]1[C@@H:11]2[C@@H:16]([CH2:17][NH:9][CH2:10]2)[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57032796(3aR,7S,7aR)-2-tert-butyloxycarbonyl-7-chloro-4,4-diphenylperhydroisoindole

Product 1

HCID 67809337(3aR,7S,7aR)-7-chloro-4,4-diphenyl-perhydroisoindole hydrochlorideYield 192.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

10 cm3 of a 6.3N solution of hydrochloric acid in dioxane are added to a solution of 1.03 g of (3aR,7S,7aR)-2-tert-butyloxycarbonyl-7-chloro-4,4-diphenylperhydroisoindole in 5 cm3 of dioxane. The reaction mixture is stirred at room temperature for 2 hours and then concentrated to dryness under reduced pressure (2.7 kPa). 0.84 g of (3aR,7S,7aR)-7-chloro-4,4-diphenyl-perhydroisoindole hydrochloride is obtained in the form of a solid which is used in the crude state in the next test.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-4163ffc9f24b4b16804dec61f2519599
Source dataset
uspto-grants-1995_09
Patent number
US05451601

Reaction notes

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