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

HRID 559307Notes

Reaction equation

HRID 559307 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([N:16]2[CH2:20][CH:19]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=3)[CH:18]([CH:29]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][N:33]=3)[CH3:30])[CH2:17]2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:28][C:23]1[CH:22]=[C:21]([CH:19]2[CH2:20][N:16]([C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[O:15])[CH2:17][CH:18]2[CH:29]([O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][N:33]=2)[CH3:30])[CH:26]=[CH:25][C:24]=1[Cl:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669996164-[(3RS,4SR)-3-[(SR)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 669991306-{(SR)-1-[(3RS,4SR)-4-(3,4-Dichloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrileYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-[(3RS,4SR)-3-[(SR)-1-(5-cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl]-piperidine-1-carboxylic acid tert-butyl ester (0.28 g, 0.50 mmol) in 24 mL of CH2Cl2 was added 6 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 0.237 g (99%) of the title compound as a white foam. ES-MS m/e: 473.0 (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-d8948189bb094285ad7a1cfe495d2f29
Source dataset
uspto-grants-2011_11
Patent number
US08063075B2

Reaction notes

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