Trifluoroacetic acid → HCID 59536633, compound

HRID 1922186Notes

Reaction equation

HRID 1922186 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]([O:18][C:19]2[C:20]([CH3:26])=[N:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH2:9]1)=O)(C)(C)C.COC1C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[Cl:25][C:22]1[N:21]=[C:20]([CH3:26])[C:19]([O:18][CH:13]([C@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:14][CH:15]2[CH2:16][CH2:17]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 59536659HCID 59536659, compound

Product 1

HCID 59536633HCID 59536633, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mix (3S)-3-[1-(6-chloro-2-methyl-3-pyridyloxy)-2-cyclopropyl-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (S-1) (0.50 g, 1.31 mmol), methoxybenzene (6.6 mL) and dichloromethane (6.6 mL) in a reaction vial. Evacuate the vial and purge with nitrogen. Add trifluoroacetic acid (1.51 g, 1.0 mL, 13.2 mmol) and stir the mixture at room temperature for 1 h. Load the mixture directly onto a pre-packed SCX column and rinse with CH2Cl2 followed by CH3OH. Elute with 2M NH3 in methanol and concentrate under reduced pressure to give 0.353 g (96%) of (3S)-3-[1-(6-chloro-2-methyl-3-pyridyloxy)-2-cyclopropyl-ethyl]-pyrrolidine (S-1). MS (m/z)=281.2 [M+1].

Workup

  1. customin a reaction vial
  2. customEvacuate the vial and
  3. custompurge with nitrogen
  4. washLoad the mixture directly onto a pre-packed SCX column and rinse with CH2Cl2
  5. washElute with 2M NH3 in methanol
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-ea5e1518bf6640e484af41688d9bb2f5
Source dataset
uspto-grants-2012_05
Patent number
US08173821B2

Reaction notes

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