HCID 12347356, compound → HCID 12347383, compound

A solution of methyl 3,3-dimethoxycyclopentanecarboxylate, methyl 3,3-dimethoxycyclopentanecarboxylate (14.68 g, 78 mmol), in THF (100 mL) was cooled (0° C. ice bath) and treated with 1.0N lithium aluminum hydride in THF (74.1 mL, 74.1 mmol) by dropwise addition. Upon completion of the addition, the reaction was warmed to room temperature and stirred for 6 hrs. The reaction was quenched by slow addition of Na2SO4-10H2O (17 g). The suspension was stirred for 1 hr, treated with anhyd. Na2SO4, and filtered. The filtrate was concentrated to afford the target compound (12.01 g, 75.0 mmol, 96% yield) as a colourless oil. 1H NMR (500 MHz, CDCl3) δ ppm 3.54 (2 H, s), 3.20 (3 H, s), 3.19 (3 H, s), 2.21-2.32 (1 H, m), 1.99 (1H, dd, J=13.28, 9.00 Hz), 1.85-1.91 (1 H, m), 1.78-1.85 (2 H, m), 1.73-1.78 (1 H, m), 1.56 (1 H, dd, J=13.12, 7.32 Hz), 1.40-1.48 (1 H, m).

1. additionUpon completion of the addition
2. customThe reaction was quenched by slow addition of Na2SO4-10H2O (17 g)
3. stirringThe suspension was stirred for 1 hr
4. additiontreated with anhyd
5. filtrationNa2SO4, and filtered
6. concentrationThe filtrate was concentrated

ORD record

ord-db002b69d771459ea54a635f5ecbc81d

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129398B2