Trifluoroacetic acid → HCID 59300132, compound

HRID 2236501Notes

Reaction equation

HRID 2236501 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]([O:15][CH3:16])[CH3:14])=O)(C)(C)C.C(O)(C(F)(F)F)=O.[N+:24]([C:27]1[CH:34]=[CH:33][C:30](CBr)=[CH:29][CH:28]=1)([O-:26])=[O:25].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:16][O:15][CH:13]([CH:9]1[CH2:10][CH2:11][CH2:12][N:8]1[CH2:6][C:30]1[CH:33]=[CH:34][C:27]([N+:24]([O-:26])=[O:25])=[CH:28][CH:29]=1)[CH3:14]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 68691414Tert-butyl 2-(1-methoxyethyl)pyrrolidine-1-carboxylate

Product 1

HCID 59300132HCID 59300132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(1-methoxy-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.0 g, 4.4 mmol) in CH2Cl2 (25 mL) is cooled to 0° C. and TFA (2.5 mL) is added dropwise. The mixture is allowed to stir at room temperature overnight. The volatiles were removed and CH3CN (20 mL) is added. After addition of 4-nitrobenzyl bromide (1.25 g, 5.78 mmol) and K2CO3 (2.0 g, 14.4 mmol) the mixture is stirred at room temperature for 5 hours. Aqueous workup followed by chromatography. (260 mg, 25%). 1H NMR (300 MHz, CDCl3) ∂8.17 (2H, d, J=8.7 Hz), 7.51 (2H, d, J=8.4 Hz), 4.29 (1H, d, J=14.4 Hz), 3.48 (1H, d, J=14.4 Hz), 3.30-3.33 (1H, m), 3.32 (3H, s), 2.88-2.91 (1H, m), 2.73-2.78 (1H, m), 2.14-2.19 (1H, m), 1.61-1.85 (4H, m), 1.15 (3H, d, J=6.6 Hz).

Workup

  1. customThe volatiles were removed
  2. additionCH3CN (20 mL) is added
  3. stirringis stirred at room temperature for 5 hours

Sources & evidence

ORD record
ord-6074f73ddd364d77959a490513b5c85d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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