methyl 3,5-dichloro-4-[(S)-3-(dimethylamino)pyrrolidin-1-ylmethyl]benzoate → 3,5-dichloro-4-[(S)-3-(dimethylamino)pyrrolidin-1-ylmethyl]benzoic acid

HRID 13755Notes

Reaction equation

HRID 13755 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:21])[C:11]=1[CH2:12][N:13]1[CH2:17][CH2:16][C@H:15]([N:18]([CH3:20])[CH3:19])[CH2:14]1)[C:5]([O:7]C)=[O:6]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:21])[C:11]=1[CH2:12][N:13]1[CH2:17][CH2:16][C@H:15]([N:18]([CH3:19])[CH3:20])[CH2:14]1)[C:5]([OH:7])=[O:6]

Participants

3

Reactant 1

HCID 68694023methyl 3,5-dichloro-4-[(S)-3-(dimethylamino)pyrrolidin-1-ylmethyl]benzoate

Product 1

HCID 686902813,5-dichloro-4-[(S)-3-(dimethylamino)pyrrolidin-1-ylmethyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

This compound was prepared in the same manner as in Reference Example 1 (step 6), except that methyl 3,5-dichloro-4-[(S)-3-(dimethylamino)pyrrolidin-1-ylmethyl]benzoate obtained in the step 3 was used and methanol was used as the solvent, and that after methanol was added to the residue and the resulting mixture was stirred, insolubles were removed by filtration and the solvent in the filtrate was distilled off under reduced pressure to obtain the objective compound.

Workup

  1. customobtained in the step 3
  2. custominsolubles were removed by filtration
  3. distillationthe solvent in the filtrate was distilled off under reduced pressure
  4. customto obtain the objective compound

Sources & evidence

ORD record
ord-b7e88198fb3f4159871c12ceae7412d9
Source dataset
uspto-grants-2010_06
Patent number
US07728131B2

Reaction notes

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