Tetrahydrofuran → tert-butyl (3R)-4-hydroxy-3-methylbutyrate

Temperature

-10 °C

Borane-dimethyl sulphide complex (10M, 10.3 ml) was added during 15 minutes to a stirred mixture of 1-tert-butyl (3R)-3-methylsuccinate (12.9 g) and THF (200 ml) which had been cooled to -10° C. and placed under an atmosphere of argon. The mixture was stirred at -10° C. for 30 minutes. The mixture was allowed to warm to room temperature and was stirred for 1 hour. The mixture was recooled to 5° C. and methanol (50 ml) was added portionwise. The mixture was allowed to warm to room temperature and was stirred for 30 minutes. The mixture was evaporated and the residue was partitioned between dichloromethane (100 ml) and water (100 ml). The organic phase was filtered through phase separating paper and evaporated to give tert-butyl (3R)-4-hydroxy-3-methylbutyrate as an oil (11 g); NMR(CDCl3) δ 3.55(2H,m), 2.1-2.4(3H,m), 1.46(9H,s), 0.98(3H,d).

1. temperatureto warm to room temperature
2. stirringwas stirred for 1 hour
3. customwas recooled to 5° C.
4. temperatureto warm to room temperature
5. stirringwas stirred for 30 minutes
6. customThe mixture was evaporated
7. customthe residue was partitioned between dichloromethane (100 ml) and water (100 ml)
8. filtrationThe organic phase was filtered through phase
9. customseparating paper
10. customevaporated

ORD record

ord-31058e969eaa41c8aed8b8e1b7559d27

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05652242