Hydrochloric Acid → 3-(4-Methoxy-benzylamino)-2-methyl-propan-1-ol

To a solution of 3-amino-2-methyl-propionic acid (5.00 g, 48.4 mmol) in tetrahydrofuran (107 ml) and 1N sodium hydroxide (107 ml, 107 mmol) was added 4-methoxybenzoyl chloride (8.69 g, 50.9 mmol) at 0° C. The mixture was stirred at room temperature for 3 hours and partitioned between water and ethyl acetate. The water phase was washed with ethyl acetate and acidified with 1N hydrochloric acid. The product was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, and concentrated in vacuo. To the residue dissolved into tetrahydrofuran (20 ml) was added 1M borane-tetrahydrofuran complex (6.40 ml, 6.40 mmol) at 0° C. The mixture was stirred at room temperature. After 30 minutes, the mixture was refluxed for 5 hours and acidified with 3N hydrochloric acid. The acidic aqueous solution was stirred at 60° C. for 2 hours. The organic solvent was evaporated under reduced pressure, then the residue was partitioned between water and ethyl acetate. The water phase was washed with ethyl acetate and basified with 3N sodium hydroxide. The product was extracted with chloroform. The organic phase was dried over sodium sulfate, and concentrated in vacuo to afford 3-(4-methoxy-benzylamino)-2-methyl-propan-1-ol as colorless oil (8.28 g, 82%).

1. custompartitioned between water and ethyl acetate
2. washThe water phase was washed with ethyl acetate
3. extractionThe product was extracted with ethyl acetate
4. dry with materialThe organic phase was dried over sodium sulfate
5. concentrationconcentrated in vacuo
6. dissolutionTo the residue dissolved into tetrahydrofuran (20 ml)
7. additionwas added 1M borane-tetrahydrofuran complex (6.40 ml, 6.40 mmol) at 0° C
8. stirringThe mixture was stirred at room temperature
9. waitAfter 30 minutes
10. temperaturethe mixture was refluxed for 5 hours
11. stirringThe acidic aqueous solution was stirred at 60° C. for 2 hours
12. customThe organic solvent was evaporated under reduced pressure
13. customthe residue was partitioned between water and ethyl acetate
14. washThe water phase was washed with ethyl acetate and basified with 3N sodium hydroxide
15. extractionThe product was extracted with chloroform
16. dry with materialThe organic phase was dried over sodium sulfate
17. concentrationconcentrated in vacuo

ORD 기록

ord-ac9b9b75e84d454fb8d92ebe3b661c9f

출처 데이터셋

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09108957B2