Lithium hydroxide, monohydrate → lithium 1-(4-methoxybenzyl)-3-(2-(quinuclidin-4-ylmethylamino)ethyl)-1H-indole-4-carboxylate

HRID 2168548Notes

Reaction equation

HRID 2168548 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([O:19]C)=[O:18])[C:11]=3[C:10]([CH2:21][CH2:22][NH:23][CH2:24][C:25]34[CH2:32][CH2:31][N:28]([CH2:29][CH2:30]3)[CH2:27][CH2:26]4)=[CH:9]2)=[CH:5][CH:4]=1.O.[OH-].[Li+:37]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([O-:19])=[O:18])[C:11]=3[C:10]([CH2:21][CH2:22][NH:23][CH2:24][C:25]34[CH2:26][CH2:27][N:28]([CH2:29][CH2:30]3)[CH2:31][CH2:32]4)=[CH:9]2)=[CH:5][CH:4]=1.[Li+:37]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66899061methyl 1-(4-methoxybenzyl)-3-(2-(quinuclidin-4-ylmethylamino)ethyl)-1H-indole-4-carboxylate

Product 1

HCID 66898816lithium 1-(4-methoxybenzyl)-3-(2-(quinuclidin-4-ylmethylamino)ethyl)-1H-indole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of methyl 1-(4-methoxybenzyl)-3-(2-(quinuclidin-4-ylmethylamino)ethyl)-1H-indole-4-carboxylate (520 mg, 1.1 mmol) from Step D above and lithium hydroxide monohydrate (142 mg, 3.4 mmol) in tetrahydrofuran/water (30 mL, 1:1) was stirred at reflux until the reaction was complete by LC-MS. The solvent was removed under reduced pressure to give lithium 1-(4-methoxybenzyl)-3-(2-(quinuclidin-4-ylmethylamino)ethyl)-1H-indole-4-carboxylate as a white solid (878 mg, crude): 1H NMR (500 MHz, CD3OD) δ 7.31 (d, J=8.0 Hz, 1H), 7.15 (d, J=7.0 Hz, 1H), 7.10-7.05 (m, 4H), 6.80 (d, J=8.5 Hz, 2H), 5.25 (s, 1H), 3.74 (s, 3H), 3.13 (t, J=7.0 Hz, 2H), 2.81 (t, J=7.0 Hz, 2H), 2.77 (t, J=7.5 Hz, 6H), 2.30 (s, 2H), 1.89 (s, 1H), 1.31 (t, J=7.5 Hz, 6H); MS (ESI+) m/z 448 (M+H).

Workup

  1. temperatureat reflux until the reaction
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8aa100c42d0d48cfaba9e0a760938f48
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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