(S)-methyl 2-((S)-1-hydroxyethyl)-5-methylhex-4-enoate → (S)-methyl 2-((S)-1-hydroxyethyl)-5-methylhexanoate

To a well stirred solution of (S)-methyl 2-((S)-1-hydroxyethyl)-5-methylhex-4-enoate (9.5 g, 51.0 mmol) in MeOH (51 mL) was added 10% Pd/C (0.543 g, 5.10 mmol). The reaction was put under a hydrogen atmosphere (balloon) and stirred at room temperature for 20 h. The mixture was filtered through a plug of Celite® and the plug was washed with MeOH (20 mL). The filtrate and washes were combined, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (50 mL). The solution was passed through a phase separator to remove residual water (H2O), and the solvent was removed under reduced pressure to afford the title compound (9.45 g, 50.2 mmol, 98%) as a slightly yellow oil: IR (thin film) 3451, 2954, 2871, 1736, 1719, 1169 cm−1; 1H NMR (400 MHz, CDCl3) δ 3.91 (p, J=6.4 Hz, 1H), 3.72 (s, 3H), 2.77 (s, 1H), 2.36 (ddd, J=9.2, 6.3, 5.0 Hz, 1H), 1.72-1.45 (m, 3H), 1.28-1.05 (m, 5H), 0.88 (dd, J=6.6, 3.2 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 176.13, 68.55, 53.29, 51.67, 36.55, 28.16, 27.37, 22.74, 22.44, 21.68.

1. filtrationThe mixture was filtered through a plug of Celite®
2. washthe plug was washed with MeOH (20 mL)
3. customthe solvent was removed under reduced pressure
4. dissolutionthe residue was dissolved in DCM (50 mL)
5. customto remove residual water (H2O)
6. customthe solvent was removed under reduced pressure

ORD record

ord-59a5b865941f4411885de22cebe2b8a9

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09247741B2