HCID 67148752, compound → HCID 86622969, compound

HRID 2428107Notes

Reaction equation

HRID 2428107 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-26384d7f5acb43fe87e1df4be07f8a0a
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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