تفاعل #986633

معادلة التفاعل

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

dimethyl 5-aminoisophthalate

propyl iodide

BH3-THF

→

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

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to rt
2. 2
   درجة الحرارةThe reaction mixture was cooled back down to 0° C.
3. 3
   أخرىcarefully quenched with MeOH
4. 4
   تركيزThe mixture was concentrated to half its original volume
5. 5
   workup.ADDITIONdiluted with EtOAc and water
6. 6
   استخلاصthe organic layer was extracted
7. 7
   غسيلwashed with sat. aq. NaHCO3 and brine
8. 8
   تجفيفdried over sodium sulfate
9. 9
   تركيزconcentrated in vacuo

الإجراء التجريبي

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).

المصدر