Pyridine → 3-[(RS)-1-(5-Chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl chloride

HRID 1158664Notes

Reaction equation

HRID 1158664 reaction equation
ClC(Cl)(OC(=O)[O:6][C:7]([Cl:10])(Cl)Cl)Cl.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH:21]([CH:23]2[CH:27]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=3)[CH2:26][NH:25][CH2:24]2)[CH3:22])=[N:18][CH:19]=1.N1C=CC=CC=1.CCOC(C)=O>C(Cl)Cl>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH:21]([CH:23]2[CH:27]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=3)[CH2:26][N:25]([C:7]([Cl:10])=[O:6])[CH2:24]2)[CH3:22])=[N:18][CH:19]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 94429TriphosgeneHCID 669991845-Chloro-2-{(RS)-1-[(3SR,4RS)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-pyridine

Product 1

HCID 866281803-[(RS)-1-(5-Chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl chlorideYield 129.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of carbonic acid ditrichloromethyl ester (triphosgene) (48 mg, 0.16 mmol) in CH2Cl2 (10 mL) at −78° C., was added a solution of 5-chloro-2-{(RS)-1-[(3SR,4RS)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-pyridine (intermediate XV-B-2) (150 mg, 0.40 mmol) and pyridine (0.072 mL, 0.88 mmol) in CH2Cl2 (5 ML) over 30 minutes. The temperature was raised to RT, and stirring was continued over night. The organic phase was washed with H2O, dried over Na2SO4. Concentration under vacuo yielded and column chromatography (SiO2, EtOAc/H, 1:1) yielded 90 mg (50%) of the title compound as a viscous colorless oil.

Workup

  1. waitwas continued over night
  2. washThe organic phase was washed with H2O
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration under vacuo
  5. customyielded

Sources & evidence

ORD record
ord-b8e57409795d46fc99e159fc763e0e85
Source dataset
uspto-grants-2010_10
Patent number
US07812021B2

Reaction notes

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