Sodium hydride → HCID 70896185, compound

HRID 2168524Notes

Reaction equation

HRID 2168524 reaction equation
Cl.Cl.[NH2:3][C@H:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.[H-].[Na+].O=[CH:15][CH2:16][N:17]1[C:21]2[C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[CH:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[N:6]12[CH2:11][CH2:10][CH:9]([CH2:8][CH2:7]1)[C@H:4]([NH:3][CH2:15][CH2:16][N:17]1[C:21]3[C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[CH:18]1)[CH2:5]2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 5049666Sodium triacetoxyborohydrideHCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochlorideHCID 86672705HCID 86672705, compound

Product 1

HCID 70896185HCID 70896185, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (S)-(−)-3-aminoquinuclidine dihydrochloride (0.2 g, 0.8 mmol) in methylene chloride (2 mL) was added sodium hydride (0.1 g, 1.6 mmol) and the mixture was stirred for 2 h. A solution of methyl 1-(2-oxoethyl)-1H-benzo[d]imidazole-7-carboxylate (0.2 g, 0.7 mmol) from Step E above in methylene chloride (3 mL) was added followed by acetic acid (0.7 mL) and the mixture was stirred at room temperature for 4 h. Sodium triacetoxyborohydride (0.4 g, 2.1 mmol) was then added in portions and the reaction was stirred at room temperature overnight. The crude reaction was quenched with methanol, concentrated under reduced pressure, and purified by preparative thin layer chromatography (90:9:1 methylene chloride/methanol/ammonium hydroxide) to afford (S)-methyl 1-(2-(quinuclidin-3-ylamino)ethyl)-1H-benzo[d]imidazole-7-carboxylate (0.2 g, quantitative yield): MS (ESI+) m/z 329 (M+H).

Workup

  1. stirringthe mixture was stirred at room temperature for 4 h
  2. stirringthe reaction was stirred at room temperature overnight
  3. customThe crude reaction
  4. customwas quenched with methanol
  5. concentrationconcentrated under reduced pressure
  6. custompurified by preparative thin layer chromatography (90:9:1 methylene chloride/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-9b29908babb640daaad3093063da1a55
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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