HCID 68505800, compound → HCID 86622968, compound

HRID 1715434Notes

Reaction equation

HRID 1715434 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH2:18][OH:19])[CH:12]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2]>CC#N.O=[Mn]=O>[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH:18]=[O:19])[CH:12]=1)[CH2:8][CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 68505800HCID 68505800, compound

Product 1

HCID 86622968HCID 86622968, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

MnO2 (475 mg, 4.92 mmol) was added to a sol. of (4-chloro-3-hydroxymethyl-benzyl)-ethyl-carbamic acid tert-butyl ester (295 mg, 0.984 mmol) in CH3CN (20 mL). The mixture was stirred at rt for 5 h and MnO2 (475 mg, 0.984 mmol) was added again. The mixture was stirred for 1 h, and the mixture was filtered over Celite, and washed with CH3CN and CH2Cl2. Evaporation of the solvents under reduced pressure yielded the crude title compound (240 mg, 82%) that was used further without purification. LC-MS: tR=1.02 min.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. filtrationthe mixture was filtered over Celite
  3. washwashed with CH3CN and CH2Cl2
  4. customEvaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-1d1a7106a6d3454c93522e1e6eb3853e
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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