Triethylamine → (S)-(-)-2-((3-Bromo-2,6-dimethoxybenzamido)methyl)-1-ethylpyrrolidine hydrochloride

HRID 224426

Reaction equation

HRID 224426 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[C:10]([O:20][CH3:21])=[C:11]([C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C:12]([OH:14])=O.S(Cl)([Cl:24])=O.C([C@H]([C@@H](C(O)=O)O)O)(O)=O.[NH2:36][CH2:37][CH:38]1[CH2:42][CH2:41][CH2:40][N:39]1[CH2:43][CH3:44]>O>[ClH:24].[CH2:43]([N:39]1[CH2:40][CH2:41][CH2:42][CH:38]1[CH2:37][NH:36][C:12](=[O:14])[C:11]1[C:15]([O:18][CH3:19])=[CH:16][CH:17]=[C:9]([Br:8])[C:10]=1[O:20][CH3:21])[CH3:44]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 27747443-Bromo-2,6-dimethoxybenzoic acidHCID 70527605HCID 70527605, compound

Product 1

HCID 15565708(S)-(-)-2-((3-Bromo-2,6-dimethoxybenzamido)methyl)-1-ethylpyrrolidine hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the same method as for compound in Example 14, except of the addition of triethylamine, this compound was prepared from 8.4 g (0.032 mol) of 3-bromo-2,6-dimethoxybenzoic acid, 20 ml of thionyl chloride and 9.0 g (0.032 mol) of (+)-2-(aminomethyl)-1-ethylpyrrolidine d-tartrate. Yield: 7.5 g, m.p. 166°-68° C., [α]D20° =10.7° (0.5% in water).

Sources & evidence

ORD record
ord-678e8210f1d94d6c960d9c3da0f045ea
Source dataset
uspto-grants-1980_11
Patent number
US04232037

Linked notes

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