tert-butyl N-[1-[3-(hydroxymethyl)phenyl]ethyl]carbamate → tert-butyl N-[1-(3-formylphenyl)ethyl]carbamate

HRID 467504Notes

Reaction equation

HRID 467504 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH:6]=[CH:7][CH:8]=1>C(Cl)Cl.O=[Mn]=O>[CH:2]([C:3]1[CH:4]=[C:5]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH:6]=[CH:7][CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 58070261tert-butyl N-[1-[3-(hydroxymethyl)phenyl]ethyl]carbamate

Product 1

HCID 72407279tert-butyl N-[1-(3-formylphenyl)ethyl]carbamateYield 82.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-[1-[3-(hydroxymethyl)phenyl]ethyl]carbamate (4.91 g, 19.54 mmol) in DCM (40 mL) was added MnO2 (13.59 g, 156.3 mmol) and the reaction mixture was stirred at ambient temperature for 48 hours. An additional portion of MnO2 (3 g 34.5 mmol) was added and the reaction mixture was stirred at ambient temperature for an additional 12 hours. The reaction mixture was filtered through a pad of Celite and the filtrate concentrated in vacuo to give the sub-title compound as a colourless oil (4.0 g, 82% Yield). 1H NMR (400 MHz, DMSO) δ 1.30-1.41 (m, 12H) 4.64-4.75 (m, 1H), 7.55 (dd, 2H), 7.64 (d, 1H), 7.78 (d, 1H), 7.83 (s, 1H) and 10.00 (s, 1H) ppm; MS (ES+) 250.5.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for an additional 12 hours
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-eeac880c6cbc41239d21c5dd6bdfa932
Source dataset
uspto-grants-2014_01
Patent number
US08623869B2

Reaction notes

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