4-Nitrophenyl chloroformate → (1S)-2,2-Dimethyl-1-{[3-(3-pyridinyl)-1H-pyrazol-1-yl]methyl}propyl 4-nitrophenyl Carbonate
Reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[C@H:3]([OH:16])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:6]1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:21]>>[C:20](=[O:21])([O:22][C:23]1[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=1)[O:16][C@H:3]([CH2:4][N:5]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:6]1)[C:2]([CH3:18])([CH3:17])[CH3:1]Participants
3
Procedure
(2S)-3,3-Dimethyl-1-[3-(3-pyridinyl)-1H-pyrazol-1-yl]-2-butanol was treated with p-nitrophenyl chloroformate as previously described in example 1g to provide the title compound as a solid foam. 1H-NMR (DMSO-d6): δ 8.97 (s, 1H), 8.46 (d, J=4 Hz, 1H), 8.13 (d, J=9 Hz, 2H), 8.10 (d, J=8 Hz, 1H), 7.9 (d, J=2 Hz, 1H), 7.38 (dd, J=7 Hz, J=4 Hz, 1H), 7.22 (d, J=9 Hz, 2H), 6.83 (d, J=2 Hz, 1H), 4.90 (d, J=9 Hz, 1H), 4.62 (d, J=14 Hz, 1H), 4.35 (dd, J=14 Hz, J=9 Hz, 1H), 1.03 (s, 9H).
Sources & evidence
- ORD record
- ord-e11fb67fc7e540e3a0a764083ec01cfe
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07288541B2
Reaction notes
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