Trifluoroacetic acid → HCID 57433451, compound

HRID 748632Notes

Reaction equation

HRID 748632 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([F:23])[CH:15]=2)[CH2:10][CH:9]1[CH2:24][OH:25])=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:23][C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=1)[O:13][CH:11]1[CH2:12][NH:8][CH:9]([CH2:24][OH:25])[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68982736HCID 68982736, compound

Product 1

HCID 57433451HCID 57433451, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2.0 g of 4-(3-fluoro-5-nitro-phenoxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (6) in 5 mL of dichloromethane was added 10 mL of TFA. The mixture was stirred for 0.5 hours at room temperature and then solvents were removed in vacuo. The resulting residue was dissolved in 50 mL of EtOAc and washed with aq. NaOH (3×25 mL) and brine (25 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated to give 1.29 g (90%) of [4-(3-fluoro-5-nitro-phenoxy)-pyrrolidin-2-yl]-methanol as a thick yellow oil, which was used directly in the following reaction.

Workup

  1. customsolvents were removed in vacuo
  2. dissolutionThe resulting residue was dissolved in 50 mL of EtOAc
  3. washwashed with aq. NaOH (3×25 mL) and brine (25 mL)
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9a3ccd76417a4444b491c11958b96de6
Source dataset
uspto-grants-2008_07
Patent number
US07399866B2

Reaction notes

Loading…