Acetic Acid → HCID 66918546, compound

A solution of (1S,2R,4S) and (1R,2S,4R)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-cyclopentanecarbonitrile (3.86 g, 10.17 mmol) in THF (20 ml) was added to a solution of TBAF (20.3 ml, 20.3 mmol, 1M solution in THF) and acetic acid (1.2 ml, 20.9 mmol) in THF (50 ml) at 0° C. After the addition was completed, the icebath was removed and the light brown solution was allowed to stir at room temperature for 3.5 h. The solution was then diluted with water and extracted 3 times with EtOAc. The combined organic layers were washed with a mixture of brine and saturated NaHCO3 solution, dried over Na2SO4 and evaporated. The remaining yellow oil was purified by silica gel chromatography (heptane/EtOAc 70:30-45:55) to obtain the title compound as yellow oil (1.29 g, 9 mmol, 90%). MS (EI): 200.3 (M+OAc)−.

1. additionAfter the addition
2. customthe icebath was removed
3. additionThe solution was then diluted with water
4. extractionextracted 3 times with EtOAc
5. washThe combined organic layers were washed with a mixture of brine and saturated NaHCO3 solution
6. dry with materialdried over Na2SO4
7. customevaporated
8. customThe remaining yellow oil was purified by silica gel chromatography (heptane/EtOAc 70:30-45:55)

ORD record

ord-be5177461f2742dbbd1724466c5ab6ca

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893099B2