Triacetoxyperiodinane → 1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinecarbaldehyde

A solution of {1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol (1.50 g, 6.66 mmol) in CH2Cl2 (50 mL) at 0° C. was treated with Dess-Martin periodinane (2.91 g, 6.66 mmol). The reaction mixture was warmed to ambient temperature and stirred overnight. The reaction was quenched with aqueous 20% Na2S2O3 (100 mL) and aqueous saturated NaHCO3 (100 mL) and then stirred for 10 minutes. The CH2Cl2 layer was separated and washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a cloudy colorless oil. The crude product was dissolved in 100 mL of 1:1 EtOAc/hexanes, filtered through a pad of silica gel, washed with 200 mL of 1:1 EtOAc/hexanes. The filtrate was concentrated to give 1.07 g (72%) of 1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinecarbaldehyde as a clear colorless oil, which was used without further purification. 1H NMR (400 MHz, CDCl3): δ 9.68 (s, 1H), 4.15-4.00 (m, 2H), 3.30-3.20 (m, 2H), 2.86 (septet, 1H, J=7.0 Hz), 2.55-2.45 (m, 1H), 2.10-1.95 (m, 2H), 1.80-1.65 (m, 2H), 1.26 (d, 6H, J=6.8 Hz).

1. customThe reaction was quenched with aqueous 20% Na2S2O3 (100 mL) and aqueous saturated NaHCO3 (100 mL)
2. stirringstirred for 10 minutes
3. customThe CH2Cl2 layer was separated
4. washwashed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customto give the crude product as a cloudy colorless oil
9. filtrationfiltered through a pad of silica gel
10. washwashed with 200 mL of 1:1 EtOAc/hexanes
11. concentrationThe filtrate was concentrated

ORD record

ord-71421e000ee24908927ea7c6e797fbee

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101634B2