Lithium borohydride → tert-Butyl N-[(1R,2S)-rel-2-(4-hydroxyphenyl)cyclopropyl]carbamate

LiBH4 (0.34 g, 15.54 mmol) was added to a solution of Pd(PPh3)4 (0.15 g, 0.13 mmol) and tert-butyl(trans)-2-[4-(allyloxy)phenyl]cyclopropylcarbamate (Intermediate I, 0.75 g, 2.59 mmol) in dry THF (20 mL) and stirred at room temperature for 1 h. After removal of the solvent, the residue was dissolved in EtOAc (25 mL), acidified with HCl (10% aqueous solution, 2 mL), and washed with water (25 mL) and brine (25 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residue was purified by column chromatography on silica gel (10%-20% EtOAc/Hexanes), affording 0.58 g of tert-butyl(trans)-2-(4-hydroxyphenyl)cyclopropylcarbamate [Rf=0.3 (30% EtOAc/Hexanes), pale yellow foam, 90% yield].

1. customAfter removal of the solvent
2. dissolutionthe residue was dissolved in EtOAc (25 mL)
3. washwashed with water (25 mL) and brine (25 mL)
4. dry with materialThe organic layer was dried over anhydrous Na2SO4
5. filtrationfiltered
6. customAfter removal of the solvent
7. customthe residue was purified by column chromatography on silica gel (10%-20% EtOAc/Hexanes)

ORD-Eintrag

ord-7efc1b8a183d4426bc66494227fa2af6

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08946296B2