Tetrahydrofuran → 2-{1-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}ethanol
Reaction equation
Br.[CH3:2][C:3]1([CH3:27])[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]2[CH:8]=[C:7]([C:15]3[N:16]=[C:17]([N:20]4[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]4)[S:18][CH:19]=3)[CH:6]=[CH:5][C:4]1=2.C([Si](C)(C)[O:33][CH2:34][CH:35]=O)(C)(C)C.C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>>[CH3:2][C:3]1([CH3:27])[CH2:12][CH2:11][C:10]([CH3:13])([CH3:14])[C:9]2[CH:8]=[C:7]([C:15]3[N:16]=[C:17]([N:20]4[CH2:25][CH2:24][CH:23]([NH:26][CH2:35][CH2:34][OH:33])[CH2:22][CH2:21]4)[S:18][CH:19]=3)[CH:6]=[CH:5][C:4]1=2Participants
5
Reactant 4
Product 1
Procedure
The preparation is carried out starting from 1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine hydrobromide and (tertbutyldimethylsilanyloxy)acetaldehyde. The protecting group is cleaved off in THF using 5 equivalent of a 1M TBAF/THF solution: The reaction mixture was stirred at room temperature for 2 h and evaporated to dryness. The product was purified by means of reversed-phase chromatography. The fractions were extracted under basic conditions, dried, filtered and evaporated.
Workup
- customevaporated to dryness
- customThe product was purified by means of reversed-phase chromatography
- extractionThe fractions were extracted under basic conditions
- customdried
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-1bfe5bac2da644279ab37adf65b6b2b7
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08907098B2
Reaction notes
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