2-Tetrahydrofuran-2-yl-aniline → (R)-2-(tetrahydrofuran-2-yl)aniline

HRID 869092Notes

Reaction equation

HRID 869092 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8]>CO>[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8]

Participants

3

Reactant 1

HCID 681089912-Tetrahydrofuran-2-yl-aniline

Product 1

HCID 68109021(R)-2-(tetrahydrofuran-2-yl)anilineYield 47.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolved 33 g of compound (4) into MeOH (265 ml) which resulted in a concentration of approximately 125 mg/ml. The mixture was filtered through a 0.2 micron membrane filter then chromatographed on a ChiralPak® IC column (30 mm×150 mm, column temp 35° C., Chiral Technologies) at 100 bar using a Berger multigram supercritical fluid chromatographic system. Mobile phase was (90:10) CO2:CH3OH eluting at 350 ml/min with UV monitoring at 220 nanometers. Obtained 15.64 g of desired product (4a) as a green oil. Analytical SFC ([90:10] CO2:CH3OH, at 5 ml/min on a ChiralPak IC column (4.6×100 mm) held at 35° C. and run at 100 bar pressure with UV monitoring at 220 nm) showed 95.5% ee with 95% overall purity.

Workup

  1. customresulted in a concentration of approximately 125 mg/ml
  2. filtrationThe mixture was filtered through a 0.2 micron membrane
  3. filtrationfilter
  4. customthen chromatographed on a ChiralPak® IC column (30 mm×150 mm, column temp 35° C., Chiral Technologies) at 100 bar

Sources & evidence

ORD record
ord-f354562055fe4f60b44535a9c86c103b
Source dataset
uspto-grants-2015_03
Patent number
US08969359B2

Reaction notes

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