Lithium hydroxide, monohydrate → HCID 66772424, compound

HRID 2370334Notes

Reaction equation

HRID 2370334 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([O:21]C)=[O:20])[C:13]=3[C:12]([CH2:23][CH2:24][NH:25][C@H:26]3[CH:31]4[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]4)[CH2:27]3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+:36]>O1CCCC1.O>[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([O-:21])=[O:20])[C:13]=3[C:12]([CH2:23][CH2:24][NH:25][C@H:26]3[CH:31]4[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]4)[CH2:27]3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+:36]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66772180HCID 66772180, compound

Product 1

HCID 66772424HCID 66772424, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 1-(phenylsulfonyl)-3-(2-(quinuclidin-3-ylamino)ethyl)-1H-indole-4-carboxylate (480 mg, 1.02 mmol) from Step D above in tetrahydrofuran (10 mL) was added lithium hydroxide monohydrate (129 mg, 3.07 mmol) in water (3 mL). The mixture was stirred at ambient temperature overnight and then concentrated under reduced pressure. The residue was dried overnight under vacuum to afford crude lithium (S)-1-(phenylsulfonyl)-3-(2-(quinuclidin-3-ylamino)ethyl)-1H-indole-4-carboxylate, which was used in the next step without further purification: MS (ESI+) m/z 454 (M+H).

Workup

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

Sources & evidence

ORD record
ord-86c3c22d5d3240cf965a93f746e65453
Source dataset
uspto-grants-2014_04
Patent number
US08710047B2

Reaction notes

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