Water → (2R,3R)-2,3-Dimethyl-hexan-1-ol

A 1M THF solution of LAH (95.9 mL, 95.9 mmol) was added to (R)-3-((2R,3R)-2,3-dimethyl-hexanoyl)-4-phenyl-oxazolidin-2-one in THF (300 mL) under nitrogen at −78° C. and stirred for 3 hours at that temperature. Water was added dropwise to quench the excess LAH and the solution was poured into a mixture of ice and ether. The mixture was extracted into ether, washed with water and dried over MgSO4. The solution was concentrated followed by the addition of excess hexane. The resulting white precipitate was filtered and washed with haxane. The filtrate was concentrated to afford the titled compound (5.05 g, 100% yield) as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 0.9 (m, 9 H) 1.0 (d, J=6.8 Hz, 1 H) 1.1 (m, 1 H) 1.2 (m, 3 H) 1.6 (m, 2 H) 3.4 (m, 1 H) 3.6 (m, 1 H).

1. customto quench the excess LAH
2. additionthe solution was poured into a mixture of ice and ether
3. extractionThe mixture was extracted into ether
4. washwashed with water
5. dry with materialdried over MgSO4
6. concentrationThe solution was concentrated
7. additionfollowed by the addition of excess hexane
8. filtrationThe resulting white precipitate was filtered
9. washwashed with haxane
10. concentrationThe filtrate was concentrated

ORD record

ord-b7c00d6a900d4859831f333159a66ec9

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07179934B2