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

HRID 40850Notes

Reaction equation

HRID 40850 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-81e127f9496449d9aeb8466bbcc41233
Source dataset
uspto-grants-2013_09
Patent number
US08530489B2

Reaction notes

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