HCID 10554040, compound → HCID 10727265, compound

A 1M nBu4NF/THF solution (8.8 ml, 8.80 mmol, 4 equivalent) was added to a THF solution (20 ml) of the compound (58) (1.13 g, 2.20 mmol), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was extracted with ethyl acetate after the addition of water. The extract was washed with brine, dried over magnesium sulfate and evaporated. The obtained crude product was purified by silica gel column chromatography (35 g, 20% AcOEt-hexane) to obtain a colorless oily product (59) (450 mg, 96%). 1H-NMR (400 MHz, CDCl3/TMS) δ: 0.99 (3/2H, d, J=6.7 Hz), 1.01 (3/2H, d, J=7.0 Hz), 1.41-1.89 (6H+1/2H, m), 1.99 (1/2H, t, J=2.7 Hz), 2.00 (1/2H, t, J=2.7 Hz), 2.13-2.19 (1/2H, m), 2.33 (1/2H, bs), 2.38 (1/2H, ddd, J=2.4, 6.1, 17.1 Hz), 2.57 (1/2H, ddd, J=2.4, 4.0, 17.1 Hz), 2.63 (1/2H, ddd, J=2.8, 4.0, 17.1 Hz), 2.72 (1/2H, ddd, J=2.8, 7.0, 17.1 Hz), 3.30-3.31 (1/2H, m), 3.41-3.56 (3/2H, m), 3.60-3.81 (2H, m>, 3.95-4.01 (3/2H, m), 4.69-4.71 (1H, m).

1. extractionThe reaction mixture was extracted with ethyl acetate
2. additionafter the addition of water
3. washThe extract was washed with brine
4. dry with materialdried over magnesium sulfate
5. customevaporated
6. customThe obtained crude product
7. customwas purified by silica gel column chromatography (35 g, 20% AcOEt-hexane)

ORD record

ord-3da114399b7d40ef846410c366315ae2

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982257B1