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

HRID 414079Notes

Reaction equation

HRID 414079 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][CH3:19])=[CH:16][CH:15]=[C:14]([Br:20])[C:13]=1[O:21]C)[CH2:2][CH3:3].[ClH:24].CC(C)=O>CCO>[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]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([Br:20])[C:13]=1[OH:21])[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 21282682(-)-N-n-propyl-2-(3-bromo-2-hydroxy-6-methoxybenzamidomethyl)pyrrolidine hydrochlorideYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 48%. M.p. (HCl) 140°-141° C. (acetone). [α]D25 =-78° C. (c=0.80, EtOH) base.

Sources & evidence

ORD record
ord-e76b91104b514909b27c0f27ca878d6c
Source dataset
uspto-grants-1988_12
Patent number
US04789683

Reaction notes

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