Trifluoroacetic acid → HCID 59536633, compound

HRID 1922175Notes

Reaction equation

HRID 1922175 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:19][CH2:18][C@H:17]([CH:20]([O:25][C:26]2[C:27]([CH3:33])=[N:28][C:29]([Cl:32])=[CH:30][CH:31]=2)[CH2:21][CH:22]2[CH2:24][CH2:23]2)[CH2:16]1)=O)(C)(C)C>COC1C=CC=CC=1.ClCCl>[Cl:32][C:29]1[N:28]=[C:27]([CH3:33])[C:26]([O:25][CH:20]([C@H:17]2[CH2:18][CH2:19][NH:15][CH2:16]2)[CH2:21][CH:22]2[CH2:23][CH2:24]2)=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59536659HCID 59536659, compound

Product 1

HCID 59536633HCID 59536633, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Add trifluoroacetic acid (1.51 g, 1.0 mL, 13.2 mmol) to a solution of (3S)-3-[1-(6-chloro-2-methyl-3-pyridyloxy)-2-cyclopropyl-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (S-1) (99.0 mg, 0.260 mmol) in methoxybenzene (1.0 mL) and dichloromethane (2.0 mL). Stir under nitrogen 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 58 mg (79%) 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. washLoad the mixture directly onto a pre-packed SCX column and rinse with CH2Cl2
  2. washElute with 2M NH3 in methanol
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-c16500e4c36d4db7970cefcc1c746c78
Source dataset
uspto-grants-2012_05
Patent number
US08173821B2

Reaction notes

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