Trifluoroacetic acid → (R)-2,5-dihydro-1H-pyrrole-2-carboxylic acid ethyl ester trifluoroacetate

HRID 1636166Notes

Reaction equation

HRID 1636166 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C@H:6]1[CH:10]=[CH:9][CH2:8][N:7]1C(OC(C)(C)C)=O)=[O:5].[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21]>>[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21].[CH2:2]([O:3][C:4]([C@H:6]1[CH:10]=[CH:9][CH2:8][NH:7]1)=[O:5])[CH3:1]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53653320(R)-2,5dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Product 1

HCID 69895296(R)-2,5-dihydro-1H-pyrrole-2-carboxylic acid ethyl ester trifluoroacetate

Procedure

(1:1) 1.5 g (0.006 mol) (R)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester were dissolved at 5° C. in 10 ml trifluoroacetic acid and stirring was continued at room temperature for 3 hours. Evaporation of the solvent in vacuo gave 2.05 g (quant.) of (R)-2,5-dihydro-1H-pyrrole-2-carboxylic acid ethyl ester trifluoroacetate (1:1) as a yellow oil. MS m/e (%): 142 (1), 68 (100), 45 (10), 41 (15). [α]D=+95.4° (c=1% in methanol).

Workup

  1. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-14a03b90c9734b8ab4c3b67a62be856b
Source dataset
uspto-grants-2003_01
Patent number
US06512001B1

Reaction notes

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