Tert-butyl 3-(3-(cycloheptylmethoxy)phenyl)-3-hydroxypropylcarbamate → Tert-butyl 3-(3-(cycloheptylmethoxy)phenyl)-3-oxopropylcarbamate

HRID 1014576Notes

Reaction equation

HRID 1014576 reaction equation
[CH:1]1([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:16]([OH:27])[CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:13]=[CH:14][CH:15]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH:1]1([CH2:8][O:9][C:10]2[CH:11]=[C:12]([C:16](=[O:27])[CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH:13]=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 67317678Tert-butyl 3-(3-(cycloheptylmethoxy)phenyl)-3-hydroxypropylcarbamateHCID 178418287HCID 178418287, compound

Product 1

HCID 67316290Tert-butyl 3-(3-(cycloheptylmethoxy)phenyl)-3-oxopropylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(3-(cycloheptylmethoxy)phenyl)-3-hydroxypropylcarbamate (0.550 g, 1.46 mmol) in dichloromethane (20 mL) was added Celite (est. 3-4 g) and pyridinium chlorochromate (0.377 g, 1.75 mmol). After stirring overnight at room temperature, the solids were removed by filtration and the filtrate was concentrated under reduced pressure. Purification by flash chromatography (5% EtOAc-hexanes) gave tert-butyl 3-(3-(cycloheptylmethoxy)phenyl)-3-oxopropylcarbamate as a clear oil. Yield (0.50 g, 91%): 1H NMR (400 MHz, DMSO-d6) δ 7.49 (d, J=7.6 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 7.39 (dd, J=4.4, 2.2 Hz, 1H), 7.18 (dd, J=7.6, 2.4 Hz, 1H), 6.78 (t, J=5.6 Hz, 1H), 3.80 (d, J=6.4 Hz, 2H), 3.24 (dt, J=6.6, 6.0 Hz, 2H), 3.10 (t, J=6.8 Hz, 2H), 1.86-1.97 (m, 1H), 1.77-1.83 (m, 2H), 1.16-1.68 (m, 19H).*

Workup

  1. customthe solids were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customPurification by flash chromatography (5% EtOAc-hexanes)

Sources & evidence

ORD record
ord-2dc0effd84a34296abe7f0e6eaa3536f
Source dataset
uspto-grants-2011_07
Patent number
US07982071B2

Reaction notes

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