Réaction #162346

Équation de réaction

Adamantane-1-carboxylic acid

4-amino-butan-2-ol

EDCI

HOBt

DIEA

→

N-(3-hydroxybutyl)adamantane-1-carboxamide

Rendement 30.2%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated
2. 2
   Autreto give a residue, which
3. 3
   Autrewas purified by preparative TLC

Mode opératoire

Adamantane-1-carboxylic acid (404 mg, 2.24 mmol), 4-amino-butan-2-ol (200 mg, 2.24 mmol), EDCI (885 mg, 4.48 mmol) and HOBt (605 mg, 4.48 mmol) were dissolved in anhydrous CH2Cl2. DIEA (1.444 g, 11.2 mmol) was added to the above mixture at 0° C. under nitrogen. The mixture was stirred overnight and concentrated to give a residue, which was purified by preparative TLC to provide N-(3-hydroxybutyl)adamantane-1-carboxamide (170 mg, 30%). 1H NMR (MeOD, 400 MHz): δ=1.20 (d, 3H), 1.66˜2.04 (m, 17H), 2.87 (m, 2H), 3.79(m, 1H).

Source