Reaction #1121789

Reaction equation

(4-fluoro-phenyl)-(5-{(S)-1-[(R)-1-(4-methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-methanone

(4-Fluoro-phenyl)-(5-{(S)-1-[(R)-1-(4-methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-methanone

→

((S)-5-pyrrolidin-2-yl-pyridin-3-yl)-methanone

Yield 109.1%

Solvents

TFA

Conditions

Workup

1. 1
   ConcentrationThe result solution is concentrated
2. 2
   Otherto remove TFA
3. 3
   workup.ADDITIONThe residue is diluted with 100 mL of CH2Cl2
4. 4
   Washby washing with 5 mL of saturated sodium bicarbonate
5. 5
   ConcentrationThe organic layer is concentrated
6. 6
   Otherpurified by flash column chromatography (CH2Cl2 100% to CH2Cl2 80% MeOH 20% gradient in 30 minutes)

Procedure

A solution of (4-fluoro-phenyl)-(5-{(S)-1-[(R)-1-(4-methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-methanone (4) (3.3 g, 8.17 mmole) in 5 mL of TFA is heated at 100° C. in a microwave reactor for 30 minutes. The result solution is concentrated to remove TFA. The residue is diluted with 100 mL of CH2Cl2, and basified by washing with 5 mL of saturated sodium bicarbonate. The organic layer is concentrated and purified by flash column chromatography (CH2Cl2 100% to CH2Cl2 80% MeOH 20% gradient in 30 minutes) to give 4-fluoro-phenyl)-((S)-5-pyrrolidin-2-yl-pyridin-3-yl)-methanone (5) (1.57 g, yield 71%) as a light brown viscose liquid.

Source