Trifluoroacetic acid → 6-{(SR)-1-[(3RS,4SR)-1-(Azetidine-3-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile

HRID 559309Notes

Reaction equation

HRID 559309 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([C:12]([N:14]2[CH2:18][C@H:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=3)[C@@H:16]([C@@H:27]([O:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][N:31]=3)[CH3:28])[CH2:15]2)=[O:13])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:9][CH:10]([C:12]([N:14]2[CH2:18][CH:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=3)[CH:16]([CH:27]([O:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][N:31]=3)[CH3:28])[CH2:15]2)=[O:13])[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 579997493-[(3R,4S)-3-[(S)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl]-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 669999286-{(SR)-1-[(3RS,4SR)-1-(Azetidine-3-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrileYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-[(3R,4S)-3-[(S)-1-(5-cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl]-azetidine-1-carboxylic acid tert-butyl ester (0.14 g, 0.25 mmol) in 4 mL of CH2Cl2 was added 1 mL of TFA. After one hour at RT, the reaction was quenched by addition of aq. NaOH 1M (until ph=10) and the product was extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrated under vacuo to yield 0.106 g (92%) of the title compound as a white foam. ES-MS m/e: 445.1 (M+H+).

Workup

  1. customthe reaction was quenched by addition of aq. NaOH 1M (until ph=10)
  2. extractionthe product was extracted with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-b2f23744fafd48179696662165d71a2e
Source dataset
uspto-grants-2011_11
Patent number
US08063075B2

Reaction notes

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