Reaction #69128

Reaction equation

(R)-tert-butyl 1-(4-hydroxyphenyl)ethylcarbamate

→

title compound

Yield 61.0%

(R)-tert-butyl 1-(4-hydroxycyclohexyl)ethylcarbamate

Yield 61.0%

Solvents

methanol

Conditions

Workup

1. 1
   FiltrationThe rhodium catalyst was filtered off
2. 2
   Concentrationthe mother liquors were concentrated in vacuo
3. 3
   OtherThe residue was purified on silica gel by flash column chromatography

Procedure

(R)-tert-butyl 1-(4-hydroxyphenyl)ethylcarbamate (described in the literature: WO 2007035154 (A1)) (100 mg, 0.4214 mmol) was dissolved in methanol (5 mL). A methanolic (5 mL) solution of rhodium on alumina (10 Wt %, 10 mg) was added. The reaction mixture was place under a hydrogen atmosphere and stir at room temperature for 18 hours. The rhodium catalyst was filtered off and the mother liquors were concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound (62 mg, 61% yield).

Source