Tert-butyl (R)-(1-(4-hydroxyphenyl)ethyl)carbamate → (R)-tert-butyl 1-(4-hydroxycyclohexyl)ethylcarbamate

HRID 887352Notes

Reaction equation

HRID 887352 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1>CO.[Rh]>[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 68668274Tert-butyl (R)-(1-(4-hydroxyphenyl)ethyl)carbamate

Product 1

HCID 59414492(R)-tert-butyl 1-(4-hydroxycyclohexyl)ethylcarbamateYield 61%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

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).

Workup

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

Sources & evidence

ORD record
ord-052111518c0740d6b6a1443605f516ac
Source dataset
uspto-grants-2012_08
Patent number
US08247421B2

Reaction notes

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