(3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochloride → HCID 118114661, compound

HRID 2284857Notes

Reaction equation

HRID 2284857 reaction equation
[NH2:1][CH:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3]1[CH:19]=[CH:18][C:6]([O:7][CH2:8][C:9]2[O:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Cl.[C:27](Cl)(=[O:37])[O:28][C@@H:29]1[CH:34]2[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]2)[CH2:30]1>N1C=CC=CC=1>[C:20]1([CH:2]([NH:1][C:27]([O:28][C@@H:29]2[CH:34]3[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]3)[CH2:30]2)=[O:37])[C:3]2[CH:19]=[CH:18][C:6]([O:7][CH2:8][C:9]3[O:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:10]=3)=[CH:5][CH:4]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 86676896(3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochlorideHCID 118114178HCID 118114178, compound

Product 1

HCID 118114661HCID 118114661, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of methyl 5-((4-(amino(phenyl)methyl)phenoxy)methyl)-furan-2-carboxylate (301 mg, 0.894 mmol) in anhydrous pyridine (5 mL) at 0° C. under nitrogen was added (R)-quinuclidin-3-yl carbonochloridate hydrochloride (243 mg, 1.07 mmol, prepared as previously reported in 16, Step 6) in one portion. The reaction was stirred at room temperature for 3 days. The reaction was quenched by addition of 10% K2CO3 solution, extracted with ethyl acetate (3×20 mL). The combined organic phases were washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified by silica gel chromatography, eluting with 0-10% 7N methanolic ammonia in ethyl acetate, to give the title compound as a yellow oil (280 mg, 64%).

Workup

  1. customprepared
  2. customThe reaction was quenched by addition of 10% K2CO3 solution
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 0-10% 7N methanolic ammonia in ethyl acetate

Sources & evidence

ORD record
ord-94ff1593560545428cc5a965d744e412
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

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