Ethyl trifluoroacetate → 2,2,2-Trifluoro-1-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]ethan-1-one

HRID 2361737Notes

Reaction equation

HRID 2361737 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][C@H:2]1[CH2:3][OH:4].[F:8][C:9]([F:16])([F:15])[C:10](OCC)=[O:11]>C1COCC1>[F:8][C:9]([F:16])([F:15])[C:10]([N:1]1[CH2:7][CH2:6][CH2:5][C@H:2]1[CH2:3][OH:4])=[O:11]

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 640091L-Prolinol2×

Product 1

HCID 186601442,2,2-Trifluoro-1-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]ethan-1-oneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

L-prolinol (2.0 g, 20 mmol) was dissolved in 20 ml of THF. On the other hand, ethyl trifluoroacetate (3.0 g, 21 mmol) was dissolved in 20 ml of THF. Then, the latter THF solution was instilled in the former THF solution containing the L-prolinol, and this was stirred for 12 hours. This reaction solution was vacuum concentrated. Thus, Compound 1 was obtained (3.7 g, yield: 97%). The result of NMR analysis with respect to this compound is shown below.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-8707bb8146aa493e8385992bf03b3113
Source dataset
uspto-grants-2014_04
Patent number
US08691782B2

Reaction notes

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