Ethyl trifluoroacetate → HCID 59651733, compound

HRID 2064098Notes

Reaction equation

HRID 2064098 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]([F:23])([F:22])[C:17](OCC)=[O:18]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:17](=[O:18])[C:16]([F:23])([F:22])[F:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 59651733HCID 59651733, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(S)-2-aminomethyl-pyrrolidine-l-carboxylic acid tert-butyl ester (10 g, 49.93 mmol) was dissolved in THF (200 ml) followed by the dropwise addition, within 5 min, of ethyl trifluoroacetate (9.75 g, 67.95 mmol) dissolved in THF (50 ml). Stirring was continued for 3 h at RT. The reaction mixture was concentrated under reduced pressure and the residue dried at HV to give the expected compound (14.86 g). LC-MS: tR=0.93 min; [M+H]−=297.29.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue dried at HV

Sources & evidence

ORD record
ord-a8c8efbe69c94538b681b55f77b096b0
Source dataset
uspto-grants-2012_10
Patent number
US08288411B2

Reaction notes

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