o-Toluenesulfonyl chloride → HCID 67100005, compound
Reaction equation
[F:1][CH:2]([F:21])[C@H:3]1[CH2:8][N:7](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:6][C@@H:5]([OH:19])[C@@H:4]1[OH:20].C1(C)C(S([Cl:31])(=O)=O)=CC=CC=1>>[ClH:31].[F:21][CH:2]([F:1])[C@H:3]1[CH2:8][NH:7][CH2:6][C@@H:5]([OH:19])[C@@H:4]1[OH:20]Participants
Procedure
(3R,4R,5S)-5-(Difluoromethyl)-1-(methanesulfonyl)piperidine 3,4-diol (8b; Z=SO2; R5=Me). Following General Procedure D except that the reaction was run at room temperature and using methanesulfonyl chloride (0.16 g, 1.4 mmol), the title compound was obtained as a white solid (0.17 g, 51%). 1H NMR (DMSO-d6) 6.2 (t, 1H, J=53 Hz), 5.43 (d, 1H, ex), 5.38 (d, 1H, ex), 3.2-3.7 (m, 4H), 2.95 (s, 3H), 2.85 (m, 1H), 2.7 (t, 1H), 2.1 (br s, 1H). (3R,4R,5S)-5-(Difluoromethyl)-1-tosylpiperidine 3,4-diol (8b; Z=SO2; R5=Ph) Following General Procedure D except that the reaction was run at room temperature and using toluenesulfonyl chloride (0.26, 1.4 mmol), the title compound was obtained as a white solid (0.35 g, 67%). 1H NMR (DMSO-d6) 7.6 (d, 2H), 7.45 (d, 2H), 6.25 (t, 1H, J=53 Hz), 5.4 (2d, 2H, ex), 3.3-3.55 (m, 4H), 3.2 (m, 1H), 2.5 (m, 3H), 2.4 (t, 1H), 2.1 (m, 1H).
Workup
- customwas run at room temperature
Sources & evidence
- ORD record
- ord-c904721e2505402fabab4cbb576a83be
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09044437B2
Reaction notes
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