Trifluoroacetic acid → (2S,4R)-N-(hex-5-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamide

HRID 1618075Notes

Reaction equation

HRID 1618075 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:14]([CH3:30])[C:15]([C@@H:17]1[CH2:21][C@@H:20]([OH:22])[CH2:19][N:18]1C(OC(C)(C)C)=O)=[O:16])[CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13]>C(Cl)Cl>[CH2:8]([N:14]([CH3:30])[C:15]([C@@H:17]1[CH2:21][C@@H:20]([OH:22])[CH2:19][NH:18]1)=[O:16])[CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57816706(2S,4R)-tert-butyl 2-(N-(hex-5-enyl)-N-methyl-carbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 57816715(2S,4R)-N-(hex-5-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid was added dropwise to a solution of compound 48 (1 g, 1 eq.) in DCM (10 mL). The reaction mixture was stirred for 3 hrs at room temperature, and then trifluoroacetic acid was removed under reduced pressure. The residue was co-evaporated with toluene to yield compound 49 as pale yellow oil in quantitative yield. MS (ESI+): m/z=227 (MH+).

Workup

  1. customtrifluoroacetic acid was removed under reduced pressure

Sources & evidence

ORD record
ord-e20d15c79e644381a62879b1f0498623
Source dataset
uspto-grants-2014_07
Patent number
US08765966B2

Reaction notes

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