2-Propanesulfonyl chloride → 2-Adamantyl 2-(isopropylsulfonyl)-2,3-dihydro-1H-spiro[isoquinoline-4,4'-piperidine]-1'-carboxylate
Reaction equation
[N:1]1([C:16]([O:18][CH:19]2[CH:26]3[CH2:27][CH:22]4[CH2:23][CH:24]([CH2:28][CH:20]2[CH2:21]4)[CH2:25]3)=[O:17])[CH2:6][CH2:5][C:4]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][NH:8][CH2:7]2)[CH2:3][CH2:2]1.[CH:29]([S:32](Cl)(=[O:34])=[O:33])([CH3:31])[CH3:30]>>[CH:29]([S:32]([N:8]1[CH2:7][C:4]2([CH2:5][CH2:6][N:1]([C:16]([O:18][CH:19]3[CH:20]4[CH2:28][CH:24]5[CH2:23][CH:22]([CH2:27][CH:26]3[CH2:25]5)[CH2:21]4)=[O:17])[CH2:2][CH2:3]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)(=[O:34])=[O:33])([CH3:31])[CH3:30]Participants
3
Procedure
The title compound was prepared from 2-adamantyl 2,3-dihydro-1H-spiro[isoquinoline-4,4′-piperidine]-1′-carboxylate following a procedure analogous to that described in Example 34 using isopropylsulfonyl chloride in place of methanesulfonyl chloride. LC-MS Method 1 tR=2.31 min, m/z=487; 1H NMR (CDCl3) δ=7.36 (d, 1H), 7.26 (t, 1H), 7.20 (t, 1H), 7.05 (d, 1H), 4.88 (s, 1H), 4.56 (br s, 2H), 4.18 (d, 2H), 4.35 (m, 1H), 2.99 (m, 4H), 1.42 (d, 6H).
Sources & evidence
- ORD record
- ord-4e9ecd9525d8434082b2618add546ec0
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927715B2
Reaction notes
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