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

HRID 1523127Notes

Reaction equation

HRID 1523127 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-c92064b1215f42f1bd2e458f053b4783
Source dataset
uspto-grants-2015_07
Patent number
US09079825B2

Reaction notes

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