Reaction #1702046

Reaction equation

Water

CDI

(R)-[4-(3-Oxo-cyclopentyl)-phenoxy]-acetic acid

Ammonium hydroxide

→

title compound

Yield 81.0%

2-[4-[(1R)-3-Oxocyclopentyl]phenoxy]acetamide

Yield 81.0%

Solvents

DMF

Conditions

Workup

1. 1
   Othera precipitate formed
2. 2
   Filtrationthe precipitate filtered off
3. 3
   Otherdried in vacuo

Procedure

(R)-[4-(3-Oxo-cyclopentyl)-phenoxy]-acetic acid (preparation 31) (1.6 mmol, 375 mg) was dissolved in DMF (3 mL), then CDI (1.84 mmol, 299 mg) was added and the reaction mixture stirred at r.t. for 90 min. Ammonium hydroxide (25% aq, 7 mL) was added and a precipitate formed. Water (7 mL) was added and the precipitate filtered off and dried in vacuo to yield the title compound (302 mg, 81%). 1H NMR (300 MHz, CDCl3) δ 7.25-7.14 (m, 2H), 6.97-6.83 (m, 2H), 6.78 (bs, 1H), 5.91 (bs, 1H), 4.49 (s, 2H), 3.52-3.28 (m, 1H), 2.77-2.57 (m, 1H), 2.57-2.11 (m, 5H), 2.09-1.79 (m, 1H).

Source