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

HRID 1158661Notes

Reaction equation

HRID 1158661 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 249%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of carbonic acid ditrichloromethyl ester (triphosgene) (22 mg, 0.074 mmol) in CH2Cl2 (3 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) (70 mg, 0.19 mmol) and pyridine (0.033 mL, 0.41 mmol) in CH2Cl2 (2 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 80 mg (98%) of the title compound as a light yellow solid.

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-7c00a1bac14c4b59830672ee3c655397
Source dataset
uspto-grants-2010_10
Patent number
US07812021B2

Reaction notes

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