Tetrahydrofuran → benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate

(1-(S)-Methyl-allyl)-carbamic acid benzyl ester (1.96 g, 9.56 mmol) was taken up in THF (200 mL). 9-BBN 0.5M in THF (38 mL, 19.0 mmol) was added slowly to the reaction mixture. The solution was allowed to stir at rt for 16 h. Quenched with H2O (65 mL), followed by 1.0M NaOH(aq) (20 mL). The solution was cooled to 0° C. in an ice bath and H2O2 30% in H2O (7.0 mL) was slowly added. The reaction was partitioned between Et2O and H2O. The layers were separated and the aqueous washed with Et2O. The combine organics were dried over Na2SO4. Solids were filtered and the solvent removed under reduced pressure. (3-hydroxy-1-(S)-methyl-propyl)-carbamic acid benzyl ester (1.85 g, 87%) was isolated by silica gel chromatography as a white solid.

1. customQuenched with H2O (65 mL)
2. temperatureThe solution was cooled to 0° C. in an ice bath
3. additionH2O2 30% in H2O (7.0 mL) was slowly added
4. customThe reaction was partitioned between Et2O and H2O
5. customThe layers were separated
6. washthe aqueous washed with Et2O
7. dry with materialThe combine organics were dried over Na2SO4
8. filtrationSolids were filtered
9. customthe solvent removed under reduced pressure

ORD record

ord-738d6d09b88c471992dadce677486f54

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569302B2