Triethylborane → N-((1S,2R)-1-(3,5-difluorobenzyl)-3-{[(4S)-6-ethyl-3,4-dihydro-2H-chromen-4-yl]amino}-2-hydroxypropyl)acetamide

Temperatur

65 °C

N-{(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(6-iodo-3,4-dihydro-2H-chromen-4-yl)amino]propyl}acetamide (1.0 g, 1.9 mmol) and Pd(dppf)Cl2 (0.078 g, 0.1 mmol) was dissolved in 20 mL of degassed THF. To the mixture was added 10 mL of 2.0 M K3PO4 followed by the addition of Et3B (3.8 mL, 3.8 mmol, 1.0 M in THF) via syringe. The reaction mixture was heated to 65° C. under a nitrogen atmosphere. After 2.5 h the reaction was determined to be complete and diluted with EtOAc (100 mL) and washed with brine (3×30 mL). The organic layer was dried over Na2SO4 and conc. in vacuo to yield brown solid. The diastereomers of the title compound were separated by preparative chiral HPLC (Chiralpak AD, 20% IPA/80% heptane, 0.1% DEA). MS (ESI+) for C23H26F2N2O3 m/z 419 (M+H)+.

1. washwashed with brine (3×30 mL)
2. dry with materialThe organic layer was dried over Na2SO4 and conc. in vacuo
3. customto yield brown solid
4. customThe diastereomers of the title compound were separated by preparative chiral HPLC (Chiralpak AD, 20% IPA/80% heptane, 0.1% DEA)

ORD-Eintrag

ord-dd6d88fbc24a48baa30a419221951aac

Quelldatensatz

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07645780B2