Trifluoroacetic acid → (S)-Benzyl pyrrolidine-3-carboxylate trifluoroacetic acid salt

HRID 928054Notes

Reaction equation

HRID 928054 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH:15]1[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59016658benzyl (S)-1-tert-butoxycarbonylpyrrolidine-3-carboxylate2×

Product 1

HCID 86713356(S)-Benzyl pyrrolidine-3-carboxylate trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.5 mL) was added to a solution of benzyl (S)-1-tert-butoxycarbonylpyrrolidine-3-carboxylate (Intermediate 192, 0.859 g) and DCM (10 mL) at room tempertaure. The mixture was stirred for 4 hours then concentrated in vacuo. The residue was azetroped with toluene then ethyl acetate to give benzyl (S)-pyrrolidine-3-carboxylate trifluoroacetic acid salt (1 g).

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-a1c1a47808554c9194699f24778aea35
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

Loading…