Aluminium lithium hydride → 2,6-Di-tert-butyl-4-[1-(4-hydroxymethyl-thiazole-2-sulfonyl)-piperidin-4-ylsulfanyl]-phenol
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([S:16][CH:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[S:27][CH:28]=[C:29]([C:31](OCC)=[O:32])[N:30]=3)(=[O:25])=[O:24])[CH2:19][CH2:18]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[C:12]([C:9]1[CH:8]=[C:7]([S:16][CH:17]2[CH2:18][CH2:19][N:20]([S:23]([C:26]3[S:27][CH:28]=[C:29]([CH2:31][OH:32])[N:30]=3)(=[O:25])=[O:24])[CH2:21][CH2:22]2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[OH:11])([CH3:15])([CH3:14])[CH3:13]Participants
3
Procedure
The title compound was prepared (116 mg, clear oil) in a manner similar to Ex. 5 from ethyl 2-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-thiazole-4-carboxylate (Ex. 19e) and LiAlH4. 1H-NMR (400 MHz, CDCl3): δ 7.51 (s, 1H), 7.23 (s, 2H), 5.31 (s, 1H), 4.84 (s, 2H), 3.80 (m, 2H), 2.90 (m, 2H), 2.42 (bs, 1H), 1.99 (m, 2H), 1.68 (m, 2H), 1.39 (s, 18H).
Sources & evidence
- ORD record
- ord-a99ed574f0024c3e826303c625cd5d2c
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897776B2
Reaction notes
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