2,6-Dimethylphenol → HCID 131731125, compound
Reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH:8]=[O:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[C:31]=1O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[C:31]=1[O:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH:8]=[O:9]Participants
Procedure
A mixture of (3-difluoromethyl-1-methyl-1H-pyrazol-4-yl)-((S)-(2-hydroxymethyl-pyrrolidin-1-yl)-methanone (2.0 g; 7.7 mmol), which was prepared as described in example P8, triphenylphosphine (2.1 g; 8.0 mmol) and 2,6-dimethylphenol (0.94 g; 7.7 mmol) in dry THF (30 ml) was cooled in an ice-bath. Diisopropyl azocarboxylate (1.60 g; 8.0 mmol) in dry THF (15 ml) was added dropwise, with stirring under nitrogen atmosphere over 10 minutes. The reaction mixture was stirred at ambient temperature for 6 hours. After removal of the solvent in vacuo, the residue (6.81 g) was purified by flash chromatography using silica gel (eluent: cyclo hexane/ethyl acetate 2:8). 1.31 g (46.8% of theory) of 3-difluoromethyl-1-methyl-1H-pyrazol-4-yl)-[(S)-2-(2,6-dimethyl-phenoxymethyl)-pyrrolidin-1-yl]-methanone (compound 1.225) was obtained in form of a white solid m.p. 137-140° C.
Workup
- customwas prepared
- temperaturewas cooled in an ice-bath
- stirringThe reaction mixture was stirred at ambient temperature for 6 hours
- customAfter removal of the solvent in vacuo
- customthe residue (6.81 g) was purified by flash chromatography
Sources & evidence
- ORD record
- ord-7450dc43f81d4eacabd0112ce50d947d
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623902B2
Reaction notes
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