Acetic Acid → {4-[4-(2-Isopropoxy-phenyl)-piperidin-1-yl]-cyclohexyl}-carbamic acid tert-butyl ester

A (4-oxo-cyclohexyl)-carbamic acid tert-butyl ester Compound 1b (1.54 g, 7.21 mmol), NaBH(OAc)3 (64.45 g, 21.0 mmol) and HOAc (0.3 mL) were added to a solution of 4-(2-isopropoxy-phenyl)-piperidine Compound 1a (1.32 g, 6.01 mmol) in CH2Cl2 (100 mL). The mixture was stirred under N2 for two days, then the reaction was quenched with MeOH. The mixture was evaporated and the resulting residue was redissolved with CH2Cl2, washed using 10% aqueous Na2CO3 and brine, then dried (Na2SO4). The crude product was purified by column chromatography to provide {4-[4-(2-isopropoxy-phenyl)-piperidin-1-yl]-cyclohexyl}-carbamic acid tert-butyl ester Compound 1c as a mixture of cis/trans isomers (MS 416; yellowish oil; 1.19 g, 48% yield).

1. customthe reaction was quenched with MeOH
2. customThe mixture was evaporated
3. dissolutionthe resulting residue was redissolved with CH2Cl2
4. washwashed
5. dry with materialdried (Na2SO4)
6. customThe crude product was purified by column chromatography

ORD-Eintrag

ord-ae5e799bd3b544039e270fad6db9d4dd

Quelldatensatz

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07470711B2