HCID 70818646, compound → HCID 86680970, compound

HRID 331526Notes

Reaction equation

HRID 331526 reaction equation
[F:1][CH2:2][CH:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH:5]=1>ClCCl.O=[Mn]=O>[F:1][CH2:2][CH:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[C:4]1[CH:5]=[CH:6][C:7]([CH:10]=[O:11])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 70818646HCID 70818646, compound

Product 1

HCID 86680970HCID 86680970, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

dioxomanganese (4.455 g, 886.4 μL, 51.24 mmol) was added to a stirred solution of tert-butyl N-[2-fluoro-1-[4-(hydroxymethyl)phenyl]ethyl]carbamate (1.15 g, 4.270 mmol) in dichloromethane (100 mL) and the reaction allowed to stir at ambient temperature for 65 hours. The reaction mixture was filtered through celite and washed with dichloromethane. The filtrate was concentrated in vacuo to give tert-butyl N-[2-fluoro-1-(4-formylphenyl)ethyl]carbamate as a colourless oil (930 mg, 82%). 1H NMR (400.0 MHz, DMSO-d6) δ 1.37 (s, 9H), 4.43-4.46 (m, 1H), 4.54-4.58 (m, 1H), 4.95-5.05 (m, 1H), 7.60 (d, 2H), 7.81 (d, 1H), 7.90 (d, 2H) and 10.00 (s, 1H) ppm; LC/MS m/z 212.0 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a653ab9a305c47218d746695e20d648c
Source dataset
uspto-grants-2014_11
Patent number
US08877759B2

Reaction notes

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