HCID 86660299, compound → (R)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate

HRID 453683Notes

Reaction equation

HRID 453683 reaction equation
C([C@@H]([O-])[C@@H](C(O)=O)[O-])(O)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C@H:19]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:20]([O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:21])=[CH:14][CH:13]=1>CCOC(C)=O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C@H:19]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:20]([O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:21])=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 86660299HCID 86660299, compound

Product 1

HCID 59401133(R)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetateYield 110.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)—((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate) (diastereomer 1 of I8) (535 mg, 1.25 mmol) was dissolved in EtOAc (250 mL) and washed with saturated Na2CO3 solution (50 ml). The organic phase was dried over Na2SO4, filtered and evaporated to give (R)—((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (490 mg; 45% yield, single diastereomer).

Workup

  1. washwashed with saturated Na2CO3 solution (50 ml)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-21b9fad7dbb64fcb95c208578d1b4706
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

Loading…