Benzoyl chloride → (R)-quinuclidin-3-yl 2-benzamido-2-(4-chlorophenyl)acetate

HRID 1619570Notes

Reaction equation

HRID 1619570 reaction equation
Cl.Cl.[NH2:3][CH:4]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1)=[O:6].C(N(CC)CC)C.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[C:30]([NH:3][CH:4]([C:16]1[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]2)[CH2:9]1)=[O:6])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67606496(R)-quinuclidin-3-yl 2-amino-2-(4-chlorophenyl)acetate dihydrochloride

Product 1

HCID 67607484(R)-quinuclidin-3-yl 2-benzamido-2-(4-chlorophenyl)acetateYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-(4-chlorophenyl)acetate dihydrochloride (I112) (0.12 g, 0.32 mmol) in DCM (5 ml), were added triethylamine (0.13 ml, 0.95 mmol) and benzoyl chloride (44.0 μl, 0.38 mmol), and the reaction was stirred at RT for 3 hours. Then the solvent was evaporated, and the residue was taken up with EtOAc and washed with Na2CO3, water and brine. The organic layer was dried over Na2SO4, filtered and evaporated to obtain (R)-quinuclidin-3-yl 2-benzamido-2-(4-chlorophenyl)acetate (0.126 g; quantitative yield).

Workup

  1. customThen the solvent was evaporated
  2. washwashed with Na2CO3, water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f7369056c8df4cd88267a66feadeb14d
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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