Trifluoroacetic acid → HCID 89686118, compound

HRID 80844Notes

Reaction equation

HRID 80844 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([O:13][CH3:14])[C@H:10]([N:15]([CH3:17])[CH3:16])[CH2:9]1)=O)(C)(C)C.[C:18]([OH:24])([C:20]([F:23])([F:22])[F:21])=[O:19]>C(Cl)Cl>[F:21][C:20]([F:23])([F:22])[C:18]([O-:24])=[O:19].[CH3:16][N:15]([CH3:17])[C@H:10]1[C@H:11]([O:13][CH3:14])[CH2:12][NH2+:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731890HCID 131731890, compound

Product 1

HCID 89686118HCID 89686118, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of racemic (trans)-tert-butyl-3-(dimethylamino)-4-methoxypyrrolidine-1-carboxylate (0.68 g, 2.8 mmol) in DCM (4.0 mL) was added TFA (2.1 mL, 28 mmol), and the reaction mixture was stirred at room temperature for 18 h. Then, the reaction mixture was concentrated under reduced pressure to provide racemic (trans)-3-(dimethylamino)-4-methoxypyrrolidin-1-ium 2,2,2-trifluoroacetate. 1H NMR (400 MHz, DEUTERIUM OXIDE) δ ppm 4.42-4.48 (m, 1 H), 3.96-4.05 (m, 2 H), 3.60 (d, J=5.4 Hz, 2 H), 3.48-3.55 (m, 1 H), 3.39 (s, 3 H), 2.97 (s, 6 H).

Workup

  1. concentrationThen, the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ef82ded3b49940d8bab107476304a6a9
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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