2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → 2-((2-Hydroxyethyl)-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-yl}amino)ethanol

HRID 1401768Notes

Reaction equation

HRID 1401768 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[CH2:34][CH:35]=[O:36])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1C[O:60][CH2:59][CH2:58]1>>[OH:60][CH2:59][CH2:58][N:26]([CH:23]1[CH2:24][CH2:25][N:20]([C:17]2[S:18][CH:19]=[C:15]([C:7]3[CH:6]=[CH:5][C:4]4[C:3]([CH3:27])([CH3:2])[CH2:12][CH2:11][C:10]([CH3:13])([CH3:14])[C:9]=4[CH:8]=3)[N:16]=2)[CH2:21][CH2:22]1)[CH2:34][CH2:35][OH:36]

Participants

4

Reactant 3

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 11078149TBAF tetrahydrofuranHCID 683809091-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine hydrobromide

Product 1

HCID 683049632-((2-Hydroxyethyl)-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-yl}amino)ethanol

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 as already described by means of a 1M TBAF/THF solution. The product was purified by means of reversed-phase chromatography and converted into the hydrochloride.

Workup

  1. customThe product was purified by means of reversed-phase chromatography

Sources & evidence

ORD record
ord-f66347cb7a4d4c7ab2fdf7167d988c59
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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