Binap, (A+-)- → (3aR,6aS)-tert-butyl 5-(5-(2-methylbenzylcarbamoyl)pyridin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

温度

95 °C

The product from Example 1C (80 mg, 0.38 mmol), the product from Example 31A (155 mg, 0.51 mmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (34 mg, 0.034 mmol), tris(dibenzylideneacetone)dipalladium(0) (10.4 mg, 0.011 mmol), and sodium tert-butoxide (54.2 mg, 0.054 mmol) were combined with toluene (5 mL). The suspension was evacuated and purged with nitrogen. The mixture was heated at 95° C. under nitrogen for 4 h. The residue was partitioned between saturated sodium bicarbonate solution(aq) (100 mL) and EtOAc (2×50 mL). The combined organic extract was washed with brine (100 mL), dried (Na2SO4) and concentrated under vacuum. The residue was purified by flash chromatography (eluted with EtOAc) on silica to provide the title compound (150 mg, 91%). MS (APCI) m/z 437 (M+H)+.

1. customThe suspension was evacuated
2. custompurged with nitrogen
3. customThe residue was partitioned between saturated sodium bicarbonate solution(aq) (100 mL) and EtOAc (2×50 mL)
4. extractionThe combined organic extract
5. washwas washed with brine (100 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated under vacuum
8. customThe residue was purified by flash chromatography (eluted with EtOAc) on silica

ORDレコード

ord-ac36c9080be1415e95c408d8adc468ad

出典データセット

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08148408B2