Reaction #1702050

Reaction equation

Methyl 4-[(1R,3S)-3-[[(1R)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]-cyclopentyl]benzoate

NaOH

→

title compound

4-[(1R,3S)-3-[[(1R)-1-(4-fluoro-3-methoxy-phenyl)ethyl]amino]-cyclopentyl]benzoic acid

Solvents

methanol

Conditions

Workup

1. 1
   OtherAfter removal of the solvent in vacuo, 2M acetic acid
2. 2
   workup.ADDITIONwas added to pH 4
3. 3
   OtherThe resulting precipitate was collected on a filter
4. 4
   Washwashed with water
5. 5
   Otherdried

Procedure

Methyl 4-[(1R,3S)-3-[[(1R)-1-(4-fluoro-3-methoxyphenyl)ethyl]amino]-cyclopentyl]benzoate (preparation 33) (89 mg) in methanol (1 mL) was treated with 2M NaOH at r.t. for 2 h. After removal of the solvent in vacuo, 2M acetic acid was added to pH 4. The resulting precipitate was collected on a filter, washed with water and dried to afford the title compound. 1H NMR (300 MHz, DMSO) δ 7.78 (d, J=8.1 Hz, 2H), 7.18 (d, J=8.2 Hz, 3H), 7.10 (dd, J=11.5, 8.3 Hz, 1H), 6.89 (ddd, J=8.2, 4.5, 1.9 Hz, 1H), 3.85-3.73 (m, 4H), 2.98-2.82 (m, 2H), 2.14-2.01 (m, 1H), 1.97-1.54 (m, 4H), 1.36 (td, J=11.7, 8.9 Hz, 1H), 1.25 (d, J=6.6 Hz, 3H).

Source