Hexane → HCID 69221993, Verbindung

Propyltriphenylphosphonium bromide (1.24 g, 3.22 mmol) in THF (10 mL) was added to hexane washed sodium hydride (123 mg, 3.22 mmol), in THF (10 mL) and stirred at room temperature for 3 h. Methyl ester 12a (P=Boc, m=2, P2=Me) (0.55 g, 2.15 mmol) in THF (5 mL) was added to the above reaction mixture slowly and then allowed to stir for additional 2 h. It was then poured into water and extracted with ethyl acetate (30 mL). The organic phase was dried with magnesium sulfate, filtered and evaporated to dryness, the resulting residue was chromatographed using 20% EtOAc in hexanes to provide the product 4-propylidene-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester. (0.100 g, 16%): MS (ESPOS): 284 [M+H]+; 1H NMR (300 MHz, CD3OD) δ 5.18 (m, m), 4.60–4.93 (m, 1), 3.91 (m, 1), 3.67 (s, 3), 2.94–3.04 (m, 2), 2.40–2.48 (m, 2), 1.99–2.06 (m, 1), 1.85–1.97 (m, 2), 1.38 (bs, 9), 0.85 (t, J=5 Hz, 3).

1. extractionextracted with ethyl acetate (30 mL)
2. dry with materialThe organic phase was dried with magnesium sulfate
3. filtrationfiltered
4. customevaporated to dryness
5. customthe resulting residue was chromatographed

ORD-Eintrag

ord-a3529b3cccd04cb9b7ca9bf9c089fb80

Quelldatensatz

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07199106B2