HCID 67155119, compound → HCID 67022355, compound

Temperature

-20 °C

To 2 (1.053 g, 4.09 mmol) in HPLC MeOH (20 mL) at −78° C. was added portion-wise KBH4 (764.3 mg, 14.2 mmol), and the resulting reaction mixture was stirred for 45 min before being warmed to −20° C., and being stirred for a further 30 min at that temperature. The mixture was then warmed to 0° C. and stirred for a further 2 h, after which the mixture was quenched with AcOH until the pH was below 7. The mixture was then concentrated in vacuo, and EtOAc (70 mL) was added followed by water (40 mL). The layers were separated and the aqueous phase was extracted with EtOAc (60 mL). The organic extracts were combined, washed with saturated brine (60 mL), dried (MgSO4) and concentrated in vacuo. Purification was performed by flash column chromatography on silica (eluant 3:7-4:6-1:1 EtOAc/Hexane) to give 3 (436 mg, 1.68 mmol, 41%) as a white solid (diastereoisomers 1:1 ratio).

1. customthe resulting reaction mixture
2. stirringbeing stirred for a further 30 min at that temperature
3. temperatureThe mixture was then warmed to 0° C.
4. stirringstirred for a further 2 h
5. customafter which the mixture was quenched with AcOH until the pH was below 7
6. concentrationThe mixture was then concentrated in vacuo, and EtOAc (70 mL)
7. additionwas added
8. customThe layers were separated
9. extractionthe aqueous phase was extracted with EtOAc (60 mL)
10. washwashed with saturated brine (60 mL)
11. dry with materialdried (MgSO4)
12. concentrationconcentrated in vacuo
13. customPurification

ORD record

ord-d8a8806e47f148f0ba49f389358019ba

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08614193B2