Trifluoroacetic acid → HCID 59299965, compound

HRID 2236498Notes

Reaction equation

HRID 2236498 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH:13]([OH:15])[CH3:14])=O)(C)(C)C.C(O)(C(F)(F)F)=O.[N+:23]([C:26]1[CH:33]=[CH:32][C:29](CBr)=[CH:28][CH:27]=1)([O-:25])=[O:24].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:6][N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[CH:13]([OH:15])[CH3:14])=[CH:28][CH:27]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 23401992Tert-butyl 2-(1-hydroxyethyl)pyrrolidine-1-carboxylate

Product 1

HCID 59299965HCID 59299965, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(1-Hydroxy-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.0 g, 4.6 mmol) in CH2Cl2 is cooled to 0° C. and TFA (2.5 mL) is added dropwise. The mixture is allowed to stir at room temperature overnight. All 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.

Workup

  1. customAll the volatiles were removed
  2. additionCH3CN (20 mL) is added
  3. stirringthe mixture is stirred at room temperature for 5 hours

Sources & evidence

ORD record
ord-615529fda7f44abba13f9e87cbc9ed46
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…