Reaktion #986633

Reaktionsgleichung

3-(methoxycarbonyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid

dimethyl 5-aminoisophthalate

propyl iodide

BH3-THF

→

methyl 3-(hydroxymethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to rt
2. 2
   TemperaturThe reaction mixture was cooled back down to 0° C.
3. 3
   Sonstigecarefully quenched with MeOH
4. 4
   EinengenThe mixture was concentrated to half its original volume
5. 5
   workup.ADDITIONdiluted with EtOAc and water
6. 6
   Extraktionthe organic layer was extracted
7. 7
   Waschenwashed with sat. aq. NaHCO3 and brine
8. 8
   Trocknendried over sodium sulfate
9. 9
   Einengenconcentrated in vacuo

Vorschrift

To a solution of: 3-(methoxycarbonyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid (12.0 g, 38.1 mmol, prepared from dimethyl 5-aminoisophthalate and propyl iodide using a similar procedure as described for the preparation of intermediate A) in THF (250 mL) cooled to 0° C. was added BH3-THF (190.3 mL, 190.3 mmol, 1 M in THF). After 10 min, the reaction mixture was allowed to warm to rt and stirred for 15 h. The reaction mixture was cooled back down to 0° C. and carefully quenched with MeOH. The mixture was concentrated to half its original volume and diluted with EtOAc and water. Following dilution, the organic layer was extracted, washed with sat. aq. NaHCO3 and brine, dried over sodium sulfate and concentrated in vacuo to provide methyl 3-(hydroxymethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.02 (s, 1H), 7.89 (s, 1H), 7.60 (s, 1H), 4.79 (d, J=5.7 Hz, 2H), 3.94 (s, 3H), 3.67 (t, J=7.2 Hz, 2H), 2.90 (s, 3H), 1.87 (br t, J=5.7 Hz, 1H), 1.55-1.45 (m, 2H), 0.92 (t, J=7.4 Hz, 3H).

Quelle