Aluminium lithium hydride → HCID 11470819, compound

Under N2 atmosphere, a solution of (3R*,10S*)-6,6,8,8,10-pentamethyl-1-oxadispiro-[2.0.5.3]dodecan-12-one (5.65 g, 22.6 mmol) in Et2O (10 mL) was added dropwise within 20 min. to a stirred suspension of lithium aluminum hydride (1.29 g, 33.8 mmol) in Et2O (25 mL). The reaction mixture was refluxed for 3 h, and then stirred at room temp. over night, prior to quenching at 0° C. by addition of water (20 mL), followed by aq. HCl (5 N, 20 mL). The organic layer was separated, the aqueous one extracted with Et2O (2×50 mL). The combined organic extracts were washed with water (50 mL) and brine (25 mL), dried (Na2SO4) and concentrated on the rotary evaporator. The resulting residue was purified by silica-gel FC (pentane/Et2O, 4:1, Rf=0.10) to provide (1R*,2S*,4R*)-1,4,7,7,9,9-hexamethylspiro[4.5]decane-1,2-diol (4.82 g, 84%).

1. temperatureThe reaction mixture was refluxed for 3 h
2. customto quenching at 0° C. by addition of water (20 mL)
3. customThe organic layer was separated
4. extractionthe aqueous one extracted with Et2O (2×50 mL)
5. washThe combined organic extracts were washed with water (50 mL) and brine (25 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated on the rotary evaporator
8. customThe resulting residue was purified by silica-gel FC (pentane/Et2O, 4:1, Rf=0.10)

ORD record

ord-d7dbac917f4c47a9a6c7c9eb1de91ee4

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07632791B2