Dimethyl Sulfoxide → 1-Methyl-3,4-dehydropiperidine-3-carboxaldehyde

Temperature

-78 °C

2.88 mL oxalyl chloride (2.4 equiv.) was dissolved in 20 mL DCM. The mixture was cooled to −78° C. and a solution of 3.37 mL DMSO (2.0 equiv.) in 10 mL DCM was added dropwise. The mixture was stirred for 15 minutes at −78° C. A solution of 3.0 g (1-Methyl-1,2,5,6-tetrahydro-pyridin-3-yl)-methanol in 10 mL DCM was added dropwise while keeping the temperature below −65° C. The mixture was stirred for 15 minutes at −78° C. 9.81 mL Triethylamine (3.0 equiv.) was added dropwise and subsequently the mixture was allowed to warm to room temperature. 50 mL DCM was added to keep the mixture stirrable. The mixture was stirred for 1 hour at room temperature. H2O was added, the organic layer was separated and the aqueous layer again extracted with DCM. The combined organic layers were dried over Na2SO4, filtrated and concentrated to yield 3.24 g of an orange oil (85% pure) which was used without further purification in the subsequent step. 1H NMR (400 MHz, CDCl3) δ 2.43 (s, 3H), 2.48-2.60 (m, 4H), 3.11-3.15 (m, 2H), 6.85 (m, 1H), 9.43 (s, 1H).

1. customthe temperature below −65° C
2. stirringThe mixture was stirred for 15 minutes at −78° C
3. temperatureto warm to room temperature
4. stirringThe mixture was stirred for 1 hour at room temperature
5. customthe organic layer was separated
6. extractionthe aqueous layer again extracted with DCM
7. dry with materialThe combined organic layers were dried over Na2SO4
8. filtrationfiltrated
9. concentrationconcentrated

ORD record

ord-b9065e476c1845b2bc94880225c53101

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722887B2