HCID 86622964, compound → HCID 86622966, compound

HRID 2428121Notes

Reaction equation

HRID 2428121 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)[CH2:8][CH2:9][F:10])([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)[CH2:8][CH2:9][F:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86622964HCID 86622964, compound

Product 1

HCID 86622966HCID 86622966, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

MnO2 (1.22 g, 12.6 mmol) was added to a sol. of (4-chloro-3-hydroxymethyl-benzyl)-(2-fluoro-ethyl)-carbamic acid tert-butyl ester (801 mg, 2.52 mmol) in CH3CN (50 mL). The mixture was stirred at rt for 4.5 h, and MnO2 (1.22 g, 12.6 mmol) was added again. The mixture was stirred for 1 h, and 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 (800 mg, quantitative yield) that was used further without purification. LC-MS: tR=1.01 min.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. filtrationwas 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-998c9bb390b046ac854e8781a053cc33
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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