Sodium hydride → HCID 20812838, compound

To a suspension of 60% NaH (2.005 g; 50.00 mmol) in anhydrous THF (100 mL), under an atmosphere of argon, was added triethyl 2-phosphonopropionate (10.73 mL; 50.00 mmol), at such a rate as to keep the reaction temperature below 30° C. The resulting mixture was stirred at room temperature for a further 1 hr. A solution of N-Boc-4-piperidone (9.965 g; 50.00 mmol), in anhydrous THF (50 mL), was added dropwise over five minutes. The resulting clear solution was stirred at ambient temperature for ˜1 hr. The reaction was quenched by the addition of water (100 mL). The resulting mixture was partitioned, the aq layer extracted once with EtOAc and the combined organics washed with saturated brine. The organics were dried over MgSO4, filtered and evaporated to a colourless oil; 14.76 g. (˜quantitative yield). This was used in the next stage without further purification. 1H NMR δ 1.19 (t, 3H), 1.36 (s, 9H), 1.77 (s, 3H), 2.25-2.37 (m, 2H), 2.51-2.56 (m, 2H), 3.22-3.44 (m, 4H), 4.11 (q, 2H). MS m/e [MH—(CO2, C4H8)]+=184.31.

1. customthe reaction temperature below 30° C
2. stirringThe resulting clear solution was stirred at ambient temperature for ˜1 hr
3. customThe reaction was quenched by the addition of water (100 mL)
4. customThe resulting mixture was partitioned
5. extractionthe aq layer extracted once with EtOAc
6. washthe combined organics washed with saturated brine
7. dry with materialThe organics were dried over MgSO4
8. filtrationfiltered
9. customevaporated to a colourless oil
10. customThis was used in the next stage without further purification

ORD record

ord-d3a8c8b8a7a24793b813c45fd1a7e603

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07795283B2