Acetone → (-)-N-n-propyl-2-(3-bromo-6-hydroxy-2-methoxybenzamidomethyl)pyrrolidine hydrochloride

HRID 414081Notes

Reaction equation

HRID 414081 reaction equation
[CH2:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][NH:10][C:11](=[O:23])[C:12]1[C:17]([O:18]C)=[CH:16][CH:15]=[C:14]([Br:20])[C:13]=1[O:21][CH3:22])[CH2:2][CH3:3].[ClH:24].CC(C)=O>CO>[ClH:24].[CH2:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][NH:10][C:11](=[O:23])[C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]([Br:20])[C:13]=1[O:21][CH3:22])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 13493825(-)-N-n-propyl-2-(3-bromo-2,6-dimethoxybenzamidomethyl)pyrrolidine

Product 1

HCID 21282684(-)-N-n-propyl-2-(3-bromo-6-hydroxy-2-methoxybenzamidomethyl)pyrrolidine hydrochlorideYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared from (-)-N-n-propyl-2-(3-bromo-2,6-dimethoxybenzamidomethyl)pyrrolidine by dealkylation in the same manner as described in Example 2. Yield 55%. M.p. (HCl) 137°-138° C. (acetone). [α]D25 =-68° C. (c=0.12; MeOH).

Sources & evidence

ORD record
ord-f550d560464c4728b7f75712a9516be3
Source dataset
uspto-grants-1988_12
Patent number
US04789683

Reaction notes

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