Hydrogen Peroxide → HCID 11447366, compound

A mixture 1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinemethanol (0.367 mol) and THF (1000 ml) was stirred at -70° C. and a solution of borane in THF (1 M) was added dropwise thereto. After the addition, the reaction mixture was allowed to warm up to room temperature and stirred at room temperature for 18 h. The reaction mixture was cooled to -10° C. and water (23 ml) was added dropwise, NaOH (3M in water, 18 ml) was added dropwise and hydrogen peroxide (30% solution in water, 28 ml) was added dropwise at the same time. Then, simultaneously, NaOH (3M in water, 36 ml) and the hydrogen peroxide (30% solution in water, 29 ml) was added dropwise. Again NaOH (50% in water, 80 ml) was added. The reaction mixture was stirred at reflux for 4 hours. The reaction mixture was cooled and filtered. The filtrate was evaporated. The resulting precipitate was dissolved in water (500 ml) and saturated with K2CO3. The product was extracted with CH2Cl2. The resulting solution was dried over MgSO4 and evaporated. The residue was crystallized from DIPE/CH3CN. After several crystallizations a total yield of 40, 8 g of (±)-trans-1-(phenylmethyl)-3-hydroxy-4-piperidinemethanol was obtained (Yield: 50.1%).

1. additionAfter the addition
2. temperatureThe reaction mixture was cooled to -10° C.
3. stirringThe reaction mixture was stirred
4. temperatureat reflux for 4 hours
5. temperatureThe reaction mixture was cooled
6. filtrationfiltered
7. customThe filtrate was evaporated
8. dissolutionThe resulting precipitate was dissolved in water (500 ml) and saturated with K2CO3
9. extractionThe product was extracted with CH2Cl2
10. dry with materialThe resulting solution was dried over MgSO4
11. customevaporated
12. customThe residue was crystallized from DIPE/CH3CN
13. customAfter several crystallizations a total yield of 40

ORD record

ord-0f6743e16b00412ea304e9d8bd2c3073

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06096761