Lithium Hydroxide → HCID 68486262, compound

HRID 16530Notes

Reaction equation

HRID 16530 reaction equation
[Br:1][C:2]1[CH:34]=[CH:33][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][N:14]([CH2:16][C@H:17]3[CH2:21][CH2:20][CH2:19][N:18]3[CH2:22][C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=3)[CH3:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][N:14]([CH2:16][C@H:17]3[CH2:21][CH2:20][CH2:19][N:18]3[CH2:22][C:23]3[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=3)[CH3:15])=[CH:9][CH:8]=2)=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68484662methyl 4-[[(R)-2-[[[[4-(4-bromophenoxy)phenyl]methyl]methylamino]methyl]-1-pyrrolidinyl]methyl]benzoate

Product 1

HCID 68486262HCID 68486262, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-[[(R)-2-[[[[4-(4-bromophenoxy)phenyl]methyl]methylamino]methyl]-1-pyrrolidinyl]methyl]benzoate in a mixture of THF and methanol and treated with an aqueous solution of lithium hydroxide (400 mg). The reaction was stirred for 3 days. After acidification with 1 N hydrochloric acid, purification by reverse phase preparative HPLC using a gradient of acetonitrile in water containing 0.1% TFA give 270 mg of 4-[[(R)-2-[[[[4-(4-bromophenoxy)phenyl]methyl]methylamino]methyl]-1-pyrrolidinyl]methyl]benzoic acid; 1NMR (400 MHz, DMSO-d6) δ 7.98 (d, 2H), 7.61 (d, 2H), 7.54 (d, 2H), 7.40 (d, 2H), 7.07 (d, 2H), 6.96 (d, 2H), 4.46 (m, 1H), 4.17 (dbr, 1H), 3.18 (m, 4H), 3.02 (m, 2H), 2.37 (sbr, 3H), 2.25 (m, 1H), 1.82 (m, 4H), 1.21 (m, 2H) ppm.

Workup

  1. customAfter acidification with 1 N hydrochloric acid, purification by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-3c7aef64082147dfb5acd5ad5b51ee36
Source dataset
uspto-grants-2010_06
Patent number
US07737145B2

Reaction notes

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