1-Piperidinecarboxaldehyde → HCID 57637386, compound

Temperature

0 °C

To 2-benzyloxymethyl-4-bromo-thiophene (29.2 g, 103 mmol, Intermediate (86)] in tetrahydrofuran (100 mL) was added dropwise a 1.8M solution of LDA in tetrahydrofuran (63 mL, 113 mmol) at 0° C. under nitrogen atmosphere. The solution was stirred at 0° C. for 30 minutes. Then N-formyl piperidine (13.75 mL, 127 mmol) was added and the reaction was stirred at 0° C. for 45 minutes, at room temperature for 15 minutes, and was quenched with saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residual oil was chromatographed through silica gel (n-heptane/ethyl acetate, 90/10 as eluant) to afford 5-benzyloxymethyl-3-bromo-thiophene-2-carbaldehyde [23.3 g, Intermediate (87)] as an orange oil.

1. stirringthe reaction was stirred at 0° C. for 45 minutes, at room temperature for 15 minutes
2. customwas quenched with saturated aqueous ammonium chloride
3. extractionThe mixture was extracted with ethyl acetate
4. dry with materialThe organic layer was dried over magnesium sulfate
5. concentrationconcentrated
6. customThe residual oil was chromatographed through silica gel (n-heptane/ethyl acetate, 90/10 as eluant)

ORD record

ord-a021d3da38814f44904512b020700862

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928231B2