Water → HCID 66899360, compound

HRID 2369856Notes

Reaction equation

HRID 2369856 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:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[C:21]([O:23]C)=[O:22])[CH:14]=[CH:13]1)[CH2:2]2.O.O.[OH-].[Li+:28]>C1COCC1>[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:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[C:21]([O-:23])=[O:22])[CH:14]=[CH:13]1)[CH2:2]2.[Li+:28]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66899159HCID 66899159, compound

Product 1

HCID 66899360HCID 66899360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-methyl 1-(2-(quinuclidin-3-ylamino)ethyl)-1H-indole-7-carboxylate (1.4 g, 4.3 mmol) from Step C above in THF (20 ml) and water (20 ml) was added lithium hydroxide monohydrate (535 mg, 12.8 mmol). The mixture was stirred at room temperature overnight and then concentrated under reduced pressure. The residue was dried overnight under vacuum to afford crude lithium (S)-1-(2-(quinuclidin-3-ylamino)ethyl)-1H-indole-7-carboxylate which was used in the next step without further purification: MS (ESI+) m/z 314 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was dried overnight under vacuum

Sources & evidence

ORD record
ord-7f2dcfb881ef4b75ab1760ee7a2f9e2f
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

Loading…