tert-Butyl hydroperoxide → N-Benzyloxycarbonyl-4-[(R*)-2-methyl-sulfinylphenyl]piperidine

Temperature

-15 °C

N-Benzyloxycarbonyl-4-[(R*)-2-methylsulfinylphenyl]-piperidine. To a solution of diethyl-D-tartarate (3.4 mL) in dichloromethane (50 mL) was added titanium tetraisopropoxide (3.0 mL) followed by water (0.18 mL). The resulting solution was stirred vigorously for 30 minutes, treated with N-benzyloxycarbony-4-(2-methylthiophenyl)piperidine (3.41 g), and cooled to -15° C. The reaction mixture was treated with tert-butylhydroperoxide (2 mL) drop wise over a period of 1 minute, and stirred at -15° C. for 40 hours. Water (4 mL) was added, and the solution was stirred vigorously for 1 hour and filtered through a bed of diatomous earth. The filtrate was stirred with 5% aqueous sodium hydroxide (100 mL) for 1 hour and was washed with brine (50 mL). The aqueous layer was extracted with dichloromethane and the combined organic layers were washed (brine), dried (anhydrous sodium sulfate), and evaporated to give a solid product which was crystallized from diisopropyl ether to afford N-Benzyloxycarbonyl-4-[(R*)-2-methyl-sulfinylphenyl]piperidine (3.0 g).

1. stirringstirred at -15° C. for 40 hours
2. stirringthe solution was stirred vigorously for 1 hour
3. filtrationfiltered through a bed of diatomous earth
4. stirringThe filtrate was stirred with 5% aqueous sodium hydroxide (100 mL) for 1 hour
5. washwas washed with brine (50 mL)
6. extractionThe aqueous layer was extracted with dichloromethane
7. washthe combined organic layers were washed (brine)
8. dry with materialdried (anhydrous sodium sulfate)
9. customevaporated
10. customto give a solid product which
11. customwas crystallized from diisopropyl ether

ORD record

ord-09f6bee192ce4085a38ebf66bdb5f85c

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05589489