Acetonitrile → Benzyl ((1S,3R)-3-aminocyclohexyl)carbamate

Benzyl N-[(1S,3R)-3-carbamoylcyclohexyl]carbamate, 18d, (9.1 g, 32.9 mmol) was suspended in a mixture of acetonitrile (100 mL) and water (100 mL) and treated with bis(trifluoroacetoxy)iodobenzene (15.5 g, 36.1 mmol). The suspension was allowed to stir at room temperature overnight and was then quenched with 1N HCl (100 mL). After evaporation of the acetonitrile, the acidic aqueous solution was washed with EtOAc (2×150 mL). The pH was adjusted to basic by addition of solid KOH and the resulting emulsion was extracted with EtOAc (3×200 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to provide product 18e (6.2 g, 75% yield).

1. customwas then quenched with 1N HCl (100 mL)
2. customAfter evaporation of the acetonitrile
3. washthe acidic aqueous solution was washed with EtOAc (2×150 mL)
4. additionbasic by addition of solid KOH
5. extractionthe resulting emulsion was extracted with EtOAc (3×200 mL)
6. dry with materialThe combined organic layers were dried over Na2SO4
7. concentrationconcentrated in vacuo

ORDレコード

ord-d17ea07f2df6453b8752cb1947ddec6f

出典データセット

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09345708B2