HCID 67148752, compound → HCID 86622969, compound

HRID 1715437Notes

Reaction equation

HRID 1715437 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH2:19][OH:20])[CH:13]=1)[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CC#N.O=[Mn]=O>[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH:19]=[O:20])[CH:13]=1)[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67148752HCID 67148752, compound

Product 1

HCID 86622969HCID 86622969, compoundYield 107.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6342AcetonitrileSolvent

Procedure

MnO2 (815 mg, 8.44 mmol) was added to a sol. of (4-chloro-3-hydroxymethyl-benzyl)-cyclopropyl-carbamic acid tert-butyl ester (526 mg, 1.69 mmol) in CH3CN (34 mL). The mixture was stirred at rt for 3 h, and was filtered over Celite, and washed with CH3CN and CH2Cl2. Evaporation of the solvents under reduced pressure yielded the crude title compound (563 mg, quantitative yield) that was used further without purification. LC-MS: tR=1.05 min; ES+: 310.04.

Workup

  1. filtrationwas filtered over Celite
  2. washwashed with CH3CN and CH2Cl2
  3. customEvaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-94ce61a68e124b498bee6bcb8ea33b21
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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