Diisobutylaluminum hydride → HCID 22860777, compound

Temperature

-78 °C

A solution of 3.72 g {13.9 mmol) of 4-benzyl-3-(R) -phenyl-2-morpholinone, prepared from (R)-phenyl-glycine as described in Example 14, in 28 mL of CH2Cl2 was cooled in a -78° C. bath under a N2 atmosphere and 14 mL of a 1.5 M solution of DIBAL-H (21 mmol) in toluene were added. After stirring the resulting solution for 0.5 h, it was allowed to warm to -50° C. and maintained at this temperature for 0.5 h. The reaction mixture was quenched by adding 10 mL of aqueous potassium sodium tartarate. The mixture was diluted with CH2Cl2 and the layers were separated. The aqueous layer was extracted 3 times with CH2Cl2. The CH2Cl2 layers were washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate furnished 3.32 g (88%) of 4-benzyl-2-(S)-hydroxy-3-(R)-phenylmorpholine suitable for use in the next step.

1. temperatureto warm to -50° C.
2. temperaturemaintained at this temperature for 0.5 h
3. customThe reaction mixture was quenched
4. additionby adding 10 mL of aqueous potassium sodium tartarate
5. additionThe mixture was diluted with CH2Cl2
6. customthe layers were separated
7. extractionThe aqueous layer was extracted 3 times with CH2Cl2
8. washThe CH2Cl2 layers were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered

ORD record

ord-11be9030ffa746cfa60af0eafa2f6222

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05512570