Water → HCID 59900540、化合物

Lithium aluminum hydride (9.2 ml, 1M in tetrahydrofuran, 9.2 mmol) was added to a solution of (2R,4R)-1-benzyl-4-methyl-2-piperidinecarboxamide (preparation 86) (3.5 g, 15.0 mmol) in tetrahydrofuran (60 ml), and the reaction heated under reflux overnight. The reaction was cooled in an ice-bath, water (0.4 ml), 15% NaOH solution (0.4 ml), and water (1.2 ml) were added consecutively, and the resulting precipitate filtered off. The filtrate was concentrated under reduced pressure, re-dissolved in dichloromethane and washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (100:0:0 to 85:15:1) to give the title compound as a yellow oil, (650 mg, 20%).

1. temperaturethe reaction heated
2. temperatureunder reflux overnight
3. temperatureThe reaction was cooled in an ice-bath
4. filtrationthe resulting precipitate filtered off
5. concentrationThe filtrate was concentrated under reduced pressure
6. dissolutionre-dissolved in dichloromethane
7. washwashed with brine
8. dry with materialdried over Na2SO4
9. customevaporated under reduced pressure
10. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane

ORDレコード

ord-ffa0ceccd83042b6a79e72eb5b6e5d80

出典データセット

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06180627B2