HCID 68506145, compound → HCID 86622959, compound

HRID 1715416Notes

Reaction equation

HRID 1715416 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([CH2:17][OH:18])[CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>CC#N.O=[Mn]=O>[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([CH:17]=[O:18])[CH:11]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68506145HCID 68506145, compound

Product 1

HCID 86622959HCID 86622959, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

MnO2 (372 mg, 3.85 mmol) was added to a sol. of (4-chloro-3-hydroxymethyl-benzyl)-methyl-carbamic acid tert-butyl ester (110 mg, 0.385 mmol) in CH3CN (7.70 mL). The mixture was stirred at rt for 4.5 h, and MnO2 (186 mg, 1.93 mmol) was added again. The mixture was stirred for 1 h, and the mixture was filtered over Celite. The precipitate was washed with CH3CN and CH2Cl2. The filtrate was evaporated under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (95 mg, 87%) that was used further without purification. LC-MS: tR=0.99 min.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. filtrationthe mixture was filtered over Celite
  3. washThe precipitate was washed with CH3CN and CH2Cl2
  4. customThe filtrate was evaporated under reduced pressure
  5. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-c223fa99b5384ee6a32991736bdd4998
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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