Water → HCID 66899496, compound

HRID 2369904Notes

Reaction equation

HRID 2369904 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][CH2:10][CH2:11][N:12]1[C:16]3[C:17]([C:21]([O:23]C)=[O:22])=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[CH:13]1)[CH2:2]2.O.[OH-].[Li+:27].O>O1CCCC1>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][CH2:10][CH2:11][N:12]1[C:16]3[C:17]([C:21]([O-:23])=[O:22])=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[CH:13]1)[CH2:2]2.[Li+:27]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 70896185HCID 70896185, compound

Product 1

HCID 66899496HCID 66899496, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-methyl 1-(2-(quinuclidin-3-ylamino)ethyl)-1H-benzo[d]imidazole-7-carboxylate (0.2 g, 0.7 mmol) from Step F above, lithium hydroxide monohydrate (0.1 g, 2.1 mmol), water (5 mL), and tetrahydrofuran (5 mL) was heated at reflux for 5 h. The reaction solution was cooled to room temperature and concentrated under reduced pressure to give lithium (S)-1-(2-(quinuclidin-3-ylamino)ethyl)-1H-benzo[d]imidazole-7-carboxylate (0.2 g): MS (ESI+) m/z 315 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0013054b411748ae90289c66053815a9
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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