Trifluoroacetic acid → HCID 54461475, compound

HRID 363211Notes

Reaction equation

[C:1]([N:4]1[CH:8](O)[CH2:7][CH:6]([CH2:10][CH3:11])[C:5]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:3])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([N:4]1[CH2:8][CH2:7][CH:6]([CH2:10][CH3:11])[C:5]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of diethyl 1-acetyl-5-hydroxy-3-ethylpyrrolidine-2,2-dicarboxylate (287 g, 0.95 mol) and triethylsilane (228 mL, 1.43 mol) in CH2Cl2 (3 L) under argon was added trifluoroacetic acid (735 mL, 9.53 mol) dropwise with stirring while maintaining the internal temperature at 25° C. by means of an ice bath. After stirring for 3 h at 23° C., the solution was concentrated in vacuo,, the residue diluted with CH2Cl2 (1.5 L), then treated with H2O (1 L) and solid Na2CO3 with vigorous stirring until the solution was basic. The organic layer was separated, dried (Na2SO4), filtered, then concentrated to give the title compound as a yellow oil (373 g) which was used without further purification.

Workup

stirringAfter stirring for 3 h at 23° C.
concentrationthe solution was concentrated in vacuo
additionthe residue diluted with CH2Cl2 (1.5 L)
additiontreated with H2O (1 L) and solid Na2CO3
stirringwith vigorous stirring until the solution
customThe organic layer was separated
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-02b7d6d86f0f4066ad2a181c689d2a0f
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05872135

Reaction notes

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