3-((Tert-butyldimethylsilyl)oxy)propanal → HCID 67322952, compound

HRID 1401772Notes

Reaction equation

HRID 1401772 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[N:15]=[C:16]([N:19]4[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20]4)[S:17][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.C([Si](C)(C)[O:31][CH2:32][CH2:33][CH:34]=O)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>>[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]3[N:15]=[C:16]([N:19]4[CH2:23][CH2:22][C@H:21]([NH:24][CH2:34][CH2:33][CH2:32][OH:31])[CH2:20]4)[S:17][CH:18]=3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 3

HCID 36623923-((Tert-butyldimethylsilyl)oxy)propanalHCID 11078149TBAF tetrahydrofuranHCID 67323334HCID 67323334, compound

Product 1

HCID 67322952HCID 67322952, compound

Procedure

The preparation is carried out starting from (S)-1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]pyrrolidin-3-ylamine and 3-(tertbutyldimethylsilanyloxy)propionaldehyde. The protecting group is cleaved off as already described by means of a 1M TBAF/THF solution. The product was purified by means of preparative HPLC and converted into the hydrochloride by treatment with methanolic HCl.

Workup

  1. customThe product was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-4f19eccf619048aaa888e3da37241c48
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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