tert-butyl 2-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)benzylcarbamate → tert-butyl 2-(4-formyl-1H-1,2,3-triazol-1-yl)benzylcarbamate

HRID 628682Notes

Reaction equation

HRID 628682 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[N:5][N:6]([C:8]2[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=2[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:7]=1>C(Cl)Cl.O=[Mn]=O>[CH:2]([C:3]1[N:4]=[N:5][N:6]([C:8]2[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=2[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:7]=1)=[O:1]

Participants

4

Reactant 1

HCID 59176464tert-butyl 2-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)benzylcarbamate

Product 1

HCID 59176518tert-butyl 2-(4-formyl-1H-1,2,3-triazol-1-yl)benzylcarbamateYield 25%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)benzylcarbamate, 13, (2.5 g, 8.31 mmol) in CH2Cl2 (10 mL) was added MnO2 (5.0 g, 57.5 mmol). The reaction mixture was stirred at room temperature for 18 h. The crude reaction mixture was then filtered through a plug of Celite® and then concentrated in vacuo. The crude material was purified by silica gel chromatography (0-5% methanol/dichloromethane) yielding 610 mg (25%) of 14: ESI+ MS: m/z (rel intensity) 225 (100, M+Na).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas then filtered through a plug of Celite®
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by silica gel chromatography (0-5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-a3990783866c4140b18ec8fe2996a17e
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

Loading…