Acetic Acid → 4-(Isopropylamino)butanol

To a solution of 4-aminobutanol (2.0 mg, 22.4 mmol) in 110 ml of dichloroethane were added acetone (3.3 ml, 44.8 mmol), acetic acid (5 eq.), and sodium acetoxyborohydride (11.9 g, 56.09 mmol). The cloudy mixture was stirred at ambient temperature for about 18 hours. The reaction was quenched with saturated sodium bicarbonate. Sodium hydroxide (1 M) was added to adjust the pH to about 10. The aqueous layer was extracted with a mixture of isopropyl alcohol and methylene chloride (1:3). The organic fractions were combined and dried over sodium sulfate, filtered, and concentrated. The desired intermediate was further purified by bulb to bulb distillation to yield 1.4 grams as a dear oil. If desired, additional yield may be recovered by extracting the aqueous fraction with 3:1 toluene:butanol.

1. customThe reaction was quenched with saturated sodium bicarbonate
2. additionSodium hydroxide (1 M) was added
3. extractionThe aqueous layer was extracted with a mixture of isopropyl alcohol and methylene chloride (1:3)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. distillationThe desired intermediate was further purified by bulb to bulb distillation
8. customto yield 1.4 grams as a dear oil
9. customadditional yield may
10. custombe recovered
11. extractionby extracting the aqueous fraction with 3:1 toluene

ORD 기록

ord-4ea4e3ae6d1f417fbf8cd74e9df2b93d

출처 데이터셋

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06245761B1